GB1351911A - Amino acid derivatives - Google Patents
Amino acid derivativesInfo
- Publication number
- GB1351911A GB1351911A GB1058572A GB1058572A GB1351911A GB 1351911 A GB1351911 A GB 1351911A GB 1058572 A GB1058572 A GB 1058572A GB 1058572 A GB1058572 A GB 1058572A GB 1351911 A GB1351911 A GB 1351911A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetoxy
- alanine
- acetyl
- alkoxyphenyl
- acetamide
- 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
- 150000003862 amino acid derivatives Chemical class 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 229960003767 alanine Drugs 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 abstract 1
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 235000004279 alanine Nutrition 0.000 abstract 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 abstract 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 abstract 1
- 229910052741 iridium Inorganic materials 0.000 abstract 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract 1
- 229960004502 levodopa Drugs 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 229910052762 osmium Inorganic materials 0.000 abstract 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/36—One oxygen atom
- C07D263/42—One oxygen atom attached in position 5
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1351911 Derivatives and precursors for preparation of DOPA MONSANTO CO 7 March 1972 [8 March 1971] 10585/72 Heading C2C [Also in Division B1] 3-(3<SP>1</SP>,4<SP>1</SP>-Dihydroxyphenyl)-L-alanine is obtained by hydrolysis of the novel compound N- acetyl- - 3 - (4<SP>1</SP> - acetoxy - 3<SP>1</SP> - alkoxyphenyl)-L- alanine obtained by asymmetric hydrogenation of α-acetamide-4-acetoxy-3-alkoxy-cinnamic acid and/or a salt thereof, e.g. using a co-ordination catalyst comprising iridium, ruthenium, osmium, palladium, platinum or rhodium and an optically active phosphine or arsine ligand. The D-isomer of N-acetyl-3(4<SP>1</SP>-acetoxy-3<SP>1</SP>-alkoxyphenyl)-4-alanine is obtained as a by-product. The novel α-acetamide-4-acetoxy-3-alkoxycinnamic acid is prepared by mild hydrolysis of 2- methyl - 4 - (4<SP>1</SP> - acetoxy - 3<SP>1</SP> - alkoxybenzyl) - 5- oxazolone obtained from 4-acetoxy-3-alkoxybenzaldehyde acetyl glycine and acetic anhydride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12218571A | 1971-03-08 | 1971-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1351911A true GB1351911A (en) | 1974-05-15 |
Family
ID=22401185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1058572A Expired GB1351911A (en) | 1971-03-08 | 1972-03-07 | Amino acid derivatives |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5239021B1 (en) |
| BE (1) | BE780324A (en) |
| CA (1) | CA1033369A (en) |
| CH (1) | CH570970A5 (en) |
| DE (1) | DE2210938C3 (en) |
| FR (1) | FR2128705B1 (en) |
| GB (1) | GB1351911A (en) |
| HU (2) | HU168826B (en) |
| IT (1) | IT1034026B (en) |
| NL (1) | NL7202928A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4376870A (en) * | 1980-12-05 | 1983-03-15 | Monsanto Company | Optically active phosphine compounds |
| EP0077099A3 (en) * | 1981-10-08 | 1983-08-03 | ANIC S.p.A. | Process for preparing amino acids and their esters |
-
1972
- 1972-03-06 NL NL7202928A patent/NL7202928A/xx unknown
- 1972-03-07 JP JP2286272A patent/JPS5239021B1/ja active Pending
- 1972-03-07 FR FR7207885A patent/FR2128705B1/fr not_active Expired
- 1972-03-07 CA CA136,469A patent/CA1033369A/en not_active Expired
- 1972-03-07 HU HUMO000823 patent/HU168826B/hu unknown
- 1972-03-07 CH CH330172A patent/CH570970A5/xx not_active IP Right Cessation
- 1972-03-07 GB GB1058572A patent/GB1351911A/en not_active Expired
- 1972-03-07 BE BE780324A patent/BE780324A/en not_active IP Right Cessation
- 1972-03-07 IT IT2153172A patent/IT1034026B/en active
- 1972-03-07 HU HU72MO930A patent/HU173252B/en unknown
- 1972-03-07 DE DE19722210938 patent/DE2210938C3/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2128705A1 (en) | 1972-10-20 |
| DE2210938C3 (en) | 1980-01-17 |
| DE2210938A1 (en) | 1972-09-14 |
| DE2210938B2 (en) | 1979-05-31 |
| NL7202928A (en) | 1972-09-12 |
| CH570970A5 (en) | 1975-12-31 |
| JPS5239021B1 (en) | 1977-10-03 |
| IT1034026B (en) | 1979-09-10 |
| CA1033369A (en) | 1978-06-20 |
| HU168826B (en) | 1976-07-28 |
| BE780324A (en) | 1972-09-07 |
| FR2128705B1 (en) | 1975-10-10 |
| HU173252B (en) | 1979-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |