GB1111752A - A novel acid anhydride,process for the manufacture and use thereof - Google Patents
A novel acid anhydride,process for the manufacture and use thereofInfo
- Publication number
- GB1111752A GB1111752A GB89966A GB89966A GB1111752A GB 1111752 A GB1111752 A GB 1111752A GB 89966 A GB89966 A GB 89966A GB 89966 A GB89966 A GB 89966A GB 1111752 A GB1111752 A GB 1111752A
- Authority
- GB
- United Kingdom
- Prior art keywords
- testosterone
- hydroxy
- androstene
- ethinyl
- vinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- 150000008065 acid anhydrides Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 6
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 abstract 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 abstract 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- CHNXZKVNWQUJIB-CEGNMAFCSA-N ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 abstract 3
- 229960000890 hydrocortisone Drugs 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- BNUOCVTVOYWNJC-HYURVVLDSA-N (8r,9s,10r,13s,14s)-10,13,17-trimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound C1CC2=CC(O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(C)(O)[C@@]1(C)CC2 BNUOCVTVOYWNJC-HYURVVLDSA-N 0.000 abstract 2
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 abstract 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 abstract 2
- -1 Alkali metal salts Chemical class 0.000 abstract 2
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 abstract 2
- 235000012000 cholesterol Nutrition 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- 229960001566 methyltestosterone Drugs 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- 229960003604 testosterone Drugs 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 abstract 1
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 abstract 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 abstract 1
- DSQNUORSFQNUMX-PWKGVDONSA-N (8S,9S,10S,11S,13S,14S)-11-hydroxy-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione Chemical class O[C@@H]1[C@@H]2[C@]3(CCC(CC3CC[C@H]2[C@@H]2C=CC([C@@]2(C)C1)=O)=O)C DSQNUORSFQNUMX-PWKGVDONSA-N 0.000 abstract 1
- IATKKATWPOVYCC-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IATKKATWPOVYCC-VMXHOPILSA-N 0.000 abstract 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 abstract 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 abstract 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 244000028419 Styrax benzoin Species 0.000 abstract 1
- 235000000126 Styrax benzoin Nutrition 0.000 abstract 1
- 235000008411 Sumatra benzointree Nutrition 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 abstract 1
- 239000006286 aqueous extract Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 229960002130 benzoin Drugs 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940107161 cholesterol Drugs 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229960005309 estradiol Drugs 0.000 abstract 1
- 229930182833 estradiol Natural products 0.000 abstract 1
- 229960003399 estrone Drugs 0.000 abstract 1
- 235000019382 gum benzoic Nutrition 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 229930007744 linalool Natural products 0.000 abstract 1
- 229940041616 menthol Drugs 0.000 abstract 1
- UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 abstract 1
- VOJYZDFYEHKHAP-XGXHKTLJSA-N norvinisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C=C)[C@@H]4[C@@H]3CCC2=C1 VOJYZDFYEHKHAP-XGXHKTLJSA-N 0.000 abstract 1
- 229940067107 phenylethyl alcohol Drugs 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 159000000001 potassium salts Chemical class 0.000 abstract 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- 229960004063 propylene glycol Drugs 0.000 abstract 1
- 235000013772 propylene glycol Nutrition 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/06—Oxalic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/36—Oxalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises methoxalic anhydride which is prepared by reacting a methoxalic acid halide with a salt of methoxalic acid. Alkali metal salts, or the salts of tertiary bases such as pyridine triethylamine, dimethylaniline or thiazole are preferred and the halide may be a chloride which is prepared by reacting potassium methoxalate with thionyl chloride. The product forms stable plate-shaped crystals MP 65-67 DEG C. and may be used as an acylating agent for hydroxy groups. The esterification process may be used for the separation of primary and secondary alcohols or for the quantitative determination of hydroxy groups. Examples describe the preparation of the anhydride, and the purification of 19-nor-17-vinyl-testosterone and linalool; the isolation of 17 - ethinyl-testosterone; the separation of estradiol from estrone; the esterification of 17-ethinyl-testosterone, methyl-testosterone, and 19 - nor - 17 - vinyl - testosterone to the corresponding methoxalates; the preparation of the potassium salts of 11b -hydroxy-androstene-3,17-dione and the 11-oxalate of hydrocortisone; the preparation and saponification of cholesterol-methoxalate and testosterone methoxalate; and the quantitative determination of the hydroxy groups in sec. octanol, phenylethyl alcohol, cyclohexanol, menthol, benzoin, propylene glycol, cholesterol, testosterone, dimethyl b -naphthyl carbinol, 17-methyl-androstene-3,17-diol, methyl testosterone, 17-vinyl-19-nor-testosterone, 17-ethinyl-testosterone, 11b - hydroxy - D 4 androstene - 3,17 - dion and hydrocortisone.ALSO:Hydroxy groups in alcohols are determined quantitatively by reacting the alcohol with methoxalic anhydride (see Division C2) dissolved in pyridine, extracting with water, and titrating the aqueous extract with sodium hydroxide alcohols mentioned are sec. octanol, propylene glycol, cholesterol, tetrosterone, dimethyl-B-naphthyl carbinol, 17-methylandrostene-3, 17-diol, methyltertosterone, 17-vinyl. 19-nor-tertosterone, 17-ethinyl-tertosterone, 11B-hydroxy-D 4-androstene-3, 17-dion and hydrocortisone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEO0010600 | 1965-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111752A true GB1111752A (en) | 1968-05-01 |
Family
ID=7352036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB89966A Expired GB1111752A (en) | 1965-01-15 | 1966-01-07 | A novel acid anhydride,process for the manufacture and use thereof |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1593190A1 (en) |
| FR (1) | FR1466671A (en) |
| GB (1) | GB1111752A (en) |
| NL (1) | NL6600508A (en) |
-
1965
- 1965-01-15 DE DE19651593190 patent/DE1593190A1/en active Pending
-
1966
- 1966-01-07 GB GB89966A patent/GB1111752A/en not_active Expired
- 1966-01-12 FR FR45580A patent/FR1466671A/en not_active Expired
- 1966-01-14 NL NL6600508A patent/NL6600508A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1466671A (en) | 1967-01-20 |
| DE1593190A1 (en) | 1970-04-30 |
| NL6600508A (en) | 1966-07-18 |
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