95063-67-5

Basic information

• Product Name: N-benzyloxycarbonyl-L-glutam-γ-propylamide t-butyl ester
• CAS NO: 95063-67-5
• Molecular Weight: 378.469
• Mol File: 95063-67-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-benzyloxycarbonyl-L-glutam-γ-propylamide t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-L-glutam-γ-propylamide t-butyl ester(95063-67-5)
• EPA Substance Registry System: N-benzyloxycarbonyl-L-glutam-γ-propylamide t-butyl ester(95063-67-5)

Safety Data

• Hazardous Substances Data: 95063-67-5(Hazardous Substances Data)

Upstream product

• 107-10-8 propylamine 
• 540-88-5 acetic acid tert-butyl ester 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 

Downstream Products

• 95064-24-7 (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-propylcarbamoyl-butyric acid tert-butyl ester 
• 95064-42-9 (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-propylcarbamoyl-butyric acid 
• 95064-02-1 (S)-2-{4-[Methyl-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-4-propylcarbamoyl-butyric acid tert-butyl ester 
• 95064-21-4 (S)-2-(4-Methylamino-benzoylamino)-4-propylcarbamoyl-butyric acid tert-butyl ester 

Relevant articles and documents

Synthesis of Monoamides of Methotrexate from L-Glutamic Acid Monoamide t-Butyl Esters

Analoques of methotrexate (amethopterin) (1) with α- or γ-monoamide functions were synthesized starting with t-butyl L-isoglutamine (12a), t-butyl L-glutamine (22a), or the appropriate N'-alkyl or N'N'-dialkyl analoques (12b-k), (22d), (22k), (22l), and (22m).The corresponding N-benzyloxycarbonyl compounds (11) and/or (21) from which the above L-glutamic acid derivatives were obtained were generally synthesized by mixed-anhydride coupling of N-benzyloxycarbonyl-L-glutamic acid (9) with the appropriate amine, conversion into the t-butyl ester, and chromatographic separation.The resulting α-monoamide γ-t-butyl ester (11) and γ-monoamide α-t-butyl ester (21) are unambiguously distinguished by mass spectrometry and 13C n.m.r. spectroscopy.Factors which affect the γ-amide/α-amide product ratio are discussed.The N-deprotected L-glutamic acid monoamide t-butyl esters (12) or (22) were individually coupled to N-trifluoroacetyl-p-methylaminobenzoic acid, and the resulting α- or γ-monoamide t-butyl esters (13) or (23) of N-(p-methyl(trifluoroacetyl)aminobenzoyl)-L-glutamic acid was hydrolysed.The N-deprotected product, viz. t-butyl N-(p-methylaminobenzoyl)-L-glutamate α- or γ-monoamide (14) or (24) was converted into the appropriate methotrexate-monoamide t-butyl ester (15) or (25), and thence the desired methotrexate-monoamide (16) or (26), by reaction with 2,4-diamino-6-bromomethylpteridine (17) or by the Taylor procedure.Features of the mass and 13C n.m.r. spectra of the intermediates are discussed.