GB970789A - Process of esterification - Google Patents
Process of esterificationInfo
- Publication number
- GB970789A GB970789A GB842762A GB842762A GB970789A GB 970789 A GB970789 A GB 970789A GB 842762 A GB842762 A GB 842762A GB 842762 A GB842762 A GB 842762A GB 970789 A GB970789 A GB 970789A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- acid
- methyl
- diethylaminoethyl
- benzoate
- 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
- 230000032050 esterification Effects 0.000 title abstract 2
- 238000005886 esterification reaction Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- -1 alkyl chloro- Chemical class 0.000 abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 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
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- GEVPHAFTDXTZHY-UHFFFAOYSA-N 2-(diethylamino)ethyl benzoate Chemical compound CCN(CC)CCOC(=O)C1=CC=CC=C1 GEVPHAFTDXTZHY-UHFFFAOYSA-N 0.000 abstract 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Natural products N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 abstract 1
- HHCVPHSEENQSLU-IWMXCVPLSA-N [(3s,8r,9s,10r,13s,14s,17s)-17-acetyloxy-10,13,17-trimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)[C@](OC(C)=O)(C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 HHCVPHSEENQSLU-IWMXCVPLSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- QFWACQSXKWRSLR-UHFFFAOYSA-N carboniodidic acid Chemical compound OC(I)=O QFWACQSXKWRSLR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229960005091 chloramphenicol Drugs 0.000 abstract 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229960005309 estradiol Drugs 0.000 abstract 1
- 229930182833 estradiol Natural products 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 abstract 1
- ZXAOWDBYBUEVKE-UHFFFAOYSA-N methyl 2-(1h-indol-2-yl)acetate Chemical compound C1=CC=C2NC(CC(=O)OC)=CC2=C1 ZXAOWDBYBUEVKE-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229960004584 methylprednisolone Drugs 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229940056360 penicillin g Drugs 0.000 abstract 1
- JDOZJEUDSLGTLU-VWUMJDOOSA-N prednisolone phosphate Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 JDOZJEUDSLGTLU-VWUMJDOOSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229960001712 testosterone propionate Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/12—Preparation of carboxylic acid esters from asymmetrical anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises (a) a process of esterification wherein an organic acid or inorganic oxyacid is reacted with a lower alkyl chloro-, bromo- or iodo-carbonate and the resulting mixed anhydride of the formula A.CO.O. COOAlkyl (I) or A1 O.CO.OAlkyl (II), wherein A is the residue of an organic acid without the carboxyl group and A1 is the residue of an inorganic acid, is reacted with the alcohol to be esterified, and (b) as new esters the diethylaminoethyl ester of 6-amino-penicillanic acid and the sodium 9a -fluoro -16- (2 and b )-methylprednisolone -21- sulphates. The preparation of the mixed anhydrides (I) and (II) is suitably carried out by addition of the halocarbonate e.g. ethyl chlorocarbonate to the acid, or its alkali-metal or alkaline earth metal salt, in an inert solvent such as dimethyl formamide, acetonitrile or acetone, at 0 DEG C. to -40 DEG C. Other specified products include ethyl benzoate, ethyl acetate, isopropyl palmitate, diethylaminoethyl benzoate, dimethylaminoethyl benzoate, diethylmalonate, diethylaminoethyl penicillin G, chloramphenicol pentothenate, chloramphenical palmitate, methyl gibrellate, methyl indolacetate, prednisolone -21- phosphate, testosterone propionate, methyl N-acetylpenicillamine, methandriol diacetate, ethyl diacetylcholate, ethyl phenaceturate and estradiol baneozate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT3814361 | 1961-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB970789A true GB970789A (en) | 1964-09-23 |
Family
ID=20081602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB842762A Expired GB970789A (en) | 1961-03-03 | 1962-03-05 | Process of esterification |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE614636A (en) |
| CH (1) | CH436239A (en) |
| DE (1) | DE1200822B (en) |
| GB (1) | GB970789A (en) |
| NL (1) | NL275507A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5874468A (en) * | 1996-12-26 | 1999-02-23 | Yissum | Brain targeted low molecular weight hydrophobic antioxidant compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1093797B (en) * | 1959-01-31 | 1960-12-01 | Bayer Ag | Process for the production of carboxylic acid esters |
| DE1111187B (en) * | 1959-11-27 | 1961-07-20 | Shell Int Research | Process for the preparation of phosphoric acid esters, phosphoric amides or carbonic anhydrides |
-
0
- NL NL275507D patent/NL275507A/xx unknown
-
1962
- 1962-02-28 CH CH243962A patent/CH436239A/en unknown
- 1962-03-01 DE DEV22113A patent/DE1200822B/en active Pending
- 1962-03-02 BE BE614636A patent/BE614636A/en unknown
- 1962-03-05 GB GB842762A patent/GB970789A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1200822B (en) | 1965-09-16 |
| BE614636A (en) | 1962-07-02 |
| CH436239A (en) | 1967-05-31 |
| NL275507A (en) |
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