5616-87-5

Basic information

• Product Name: L-Valine, N-Methyl-, 1,1-diMethylethyl ester
• Synonyms: L-Valine, N-Methyl-, 1,1-diMethylethyl ester;N-Methyl-(S)-valin-tert-butylester;N-methyl-L-valine t-butyl ester
• CAS NO: 5616-87-5
• Molecular Formula: C₁₀H₂₁NO₂
• Molecular Weight: 187.27924
• Mol File: 5616-87-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 32 °C(Press: 0.2 Torr)
• Appearance: /
• Density: 0.906±0.06 g/cm3(Predicted)
• PKA: 7.65±0.30(Predicted)
• CAS DataBase Reference: L-Valine, N-Methyl-, 1,1-diMethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Valine, N-Methyl-, 1,1-diMethylethyl ester(5616-87-5)
• EPA Substance Registry System: L-Valine, N-Methyl-, 1,1-diMethylethyl ester(5616-87-5)

Safety Data

• Hazardous Substances Data: 5616-87-5(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 270261-55-7 2-[(benzothiazole-2-sulfonyl)-methyl-amino]-3-methyl-butyric acid tert-butyl ester 

Downstream Products

• 5616-88-6 benzyloxycarbonylsarcosyl-N-methylvaline t-butyl ester 
• 889872-66-6 O-Benzyloxycarbonyl-D-α-hydroxy-isovaleryl-N-methyl-L-valin-tert.-butylester 
• 89537-02-0 Z-(Me)Leu-(Me)Val-O-(t-Bu) 
• 131226-12-5 t-Butyl N-methyl-N-<4-<1-<(4-methylphenyl)sulfonyl>-2-pyrrolyl>-4-oxobutanoyl>-L-valinate 
• 226066-16-6 C₁₂H₁₅Cl₂NO₄S 
• 89537-04-2 N-(Benzyloxycarbonyl)-N-methyl-(S)-leucyl-N-methyl-(S)-leucyl-N-methyl-(S)-valin-tert-butylester 
• 21148-64-1 (2-nitro-3-hydroxy-4-methylbenzoyl)treonyl-D-valylprolylsarcosyl-N-methylvaline(treonine hydroxyl) lactone 
• 73984-46-0 benzyloxycarbonylsarcosyl-N-methylvaline 
• 109745-94-0 N-(tert-Butoxycarbonyl)-(R)-alanyl-N-Methyl-(S)-leucyl-N-methyl-(S)-leucyl-N-methyl-(S)-valin 
• 109745-94-0 N-(Benzyloxycarbonyl)tetrapeptidsaeure 
• 109745-92-8 N-(Benzyloxycarbonyl)-(R)-alanyl-N-Methyl-(S)-leucyl-N-methyl-(S)-leucyl-N-methyl-(S)-valin-tert-butylester 
• 117194-63-5 Z-(Me)Leu-Ala-D-Ala-(Me)Leu-(Me)Leu-(Me)Val-O-(t-Bu) 
• 117194-54-4 Z-(Me)Leu-Val-(Me)Leu-Ala-D-Ala-(Me)Leu-(Me)Leu-(Me)Val-O-(t-Bu) 
• 117194-59-9 Z-Ala-D-Ala-(Me)Leu-(Me)Leu-(Me)Val-O-(t-Bu) 

Relevant articles and documents

Solution-phase synthesis of a hindered N-methylated tetrapeptide using Bts-protected amino acid chlorides: Efficient coupling and methylation steps allow purification by extraction

N-Benzothiazole-2-sulfonyl (Bts)-protected amino acid chlorides were used to prepare the hindered cyclosporin 8-11 tetrapeptide subunit 1. The synthesis was performed via 3a and the deprotected amines 5a, 13, and 19, including three repeated cycles involving N-methylation using iodomethane/potassium carbonate, deprotection of the Bts group, and N- acylation with a N-Bts-amino acid chloride such as 9b or 9c. Among three Bts cleavage methods compared (H3PO2/THF; NaBH4/EtOH; PhSH/K2CO3), the third gave somewhat higher overall yields. N-Acylation of 5a with the Bts-protected N-methylamino acid chloride 10b followed by deprotection was also highly efficient and could be used as an alternative route to 11. Each of the deprotected amines was isolated without chromatography using simple extraction methods to remove neutral byproducts. The tetrapeptide 1 was obtained in analytically pure form as the monohydrate.