GB1038913A - A process for producing n-carboxy anhydrides of alpha-amino acids - Google Patents

A process for producing n-carboxy anhydrides of alpha-amino acids

Info

Publication number
GB1038913A
GB1038913A GB4526463A GB4526463A GB1038913A GB 1038913 A GB1038913 A GB 1038913A GB 4526463 A GB4526463 A GB 4526463A GB 4526463 A GB4526463 A GB 4526463A GB 1038913 A GB1038913 A GB 1038913A
Authority
GB
United Kingdom
Prior art keywords
temperature
amino acids
dioxan
reaction solvent
reaction
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
Application number
GB4526463A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Asahi Kasei Corp
Asahi Chemical Industry Co Ltd
Original Assignee
Asahi Chemical Industry Co Ltd
Asahi Kasei Kogyo KK
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Asahi Chemical Industry Co Ltd, Asahi Kasei Kogyo KK filed Critical Asahi Chemical Industry Co Ltd
Publication of GB1038913A publication Critical patent/GB1038913A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D263/44—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems

Abstract

N-Carboxy anhydrides of amino acids of the general formula <FORM:1038913/C2/1> in which R1 and R2 represent a hydrogen atom or a hydrocarbon group which may be substituted or they may be connected to form a ring together with the carbon atom to which they are attached, are obtained by reacting amino acids with phosgene in a reaction solvent, distilling off the reaction solvent at a temperature between -40 DEG and 40 DEG C., until 1-2 c.c. of the reaction solvent per gram of the a -amino acid used is left, separating crystals of N-carboxy anhydride product and then drying the same. The reaction temperature and the temperature at which excess phosgene is removed is generally in the range from 10 DEG to 65 DEG C. The temperature of the recrystallization step is preferably less than 30 DEG C. The product is preferably dried at a temperature below 60 DEG C. and also under reduced pressure. Suitable reaction solvents are 1,4-dioxan; 1,3-dioxan; 4,4-dimethyl-1,3-dioxan; tetrahydrofuran, methylene chloride; 1,2-dichloroethane and acetonitrile. Suitable amino acids for use in the process include glycine, alanine, phenylalanine, leucine, isoleucine, valine, aspartic acid glutamic acid, a -amino adipic acid, ornithine, lysine, arginine, cystine, methionine. Examples are given for the production of N-carboxy anhydrides of L-alanine, g -methyl-L-glutamate and L-leucine.
GB4526463A 1962-11-16 1963-11-15 A process for producing n-carboxy anhydrides of alpha-amino acids Expired GB1038913A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP5008562 1962-11-16

Publications (1)

Publication Number Publication Date
GB1038913A true GB1038913A (en) 1966-08-10

Family

ID=12849169

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4526463A Expired GB1038913A (en) 1962-11-16 1963-11-15 A process for producing n-carboxy anhydrides of alpha-amino acids

Country Status (1)

Country Link
GB (1) GB1038913A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1015169C2 (en) * 2000-05-12 2001-11-13 Dsm Nv Process for the preparation of N-carboxy-t-leucine anhydride.
EP1262480A1 (en) * 2001-05-31 2002-12-04 Isochem Process for the preparation of N-carboxyanhydrides of amino acids
KR100814266B1 (en) * 2001-05-31 2008-03-18 이소켐 Process for the preparation of N-carboxyanhydrides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1015169C2 (en) * 2000-05-12 2001-11-13 Dsm Nv Process for the preparation of N-carboxy-t-leucine anhydride.
EP1153923A1 (en) * 2000-05-12 2001-11-14 Dsm N.V. Process for the preparation of N-Carboxy-t-Leucine anhydride
US6476231B2 (en) 2000-05-12 2002-11-05 Dsm N.V. Process for the preparation of N-carboxy-t-leucine anhydride
EP1262480A1 (en) * 2001-05-31 2002-12-04 Isochem Process for the preparation of N-carboxyanhydrides of amino acids
FR2828195A1 (en) * 2001-05-31 2003-02-07 Isochem Sa Process for the preparation of N-carboxyanhydrides
US6603016B2 (en) * 2001-05-31 2003-08-05 Isochem Process for the preparation of N-carboxyanhydrides
KR100814266B1 (en) * 2001-05-31 2008-03-18 이소켐 Process for the preparation of N-carboxyanhydrides

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