127556-12-1

Basic information

• Product Name: N-<(S)-2'-amino-3-phenylpropanoyl>bornane-2,10-sultam hydrochloride
• Synonyms: N-<(S)-2'-amino-3-phenylpropanoyl>bornane-2,10-sultam hydrochloride
• CAS NO: 127556-12-1
• Molecular Weight: 398.954
• Mol File: 127556-12-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-<(S)-2'-amino-3-phenylpropanoyl>bornane-2,10-sultam hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-<(S)-2'-amino-3-phenylpropanoyl>bornane-2,10-sultam hydrochloride(127556-12-1)
• EPA Substance Registry System: N-<(S)-2'-amino-3-phenylpropanoyl>bornane-2,10-sultam hydrochloride(127556-12-1)

Safety Data

• Hazardous Substances Data: 127556-12-1(Hazardous Substances Data)

Upstream product

• 620-05-3 iodomethylbenzene 
• 94594-90-8 (2R)-bornane-10,2-sultam 
• 127556-03-0 (2R)-N-{N'-[bis(methylthio)methylidine]glycyl}bornane-10,2-sultam 
• 138566-18-4 (S)-2-(Benzhydrylidene-amino)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-phenyl-propan-1-one 
• 127556-05-2 (2R)-N-<(2S)-2-<amino>-3-phenylpropan-1-oyl>bornane-10,2-sultam 

Downstream Products

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 17585-69-2 L-phenylalanine hydrochloride 
• 63-91-2 L-phenylalanine 

Relevant articles and documents

Asymmetric alkylations of a sultam-derived glycine equivalent: Practical preparation of enantiomerically pure α-amino acids

Alkylation of the chiral glycine derivative 2 with 'activated' organohalides under ultrasound-assisted phase-transfer catalysis or with activated and nonactivatcd organohalides in anhydrous medium provides (mostly crystalline) alkylation products 3. Acidic hydrolysis of the pure products 3 gives (aminoacyl)sultams 4 which by mild saponification furnish pure α-amino acids 5 in good overall yields from 2, along with recovered auxiliary 1 (Scheme 1). Pure ω-protected α,ω-diamino acids and α-amino-ω-(hydroxyamino)acids 12-16 are readily accessible from (ω-haloacyl)sultams 3 via reaction with N-nucleophiles followed by acidic and basic hydrolyses (Scheme 2). A reliable determination of the enantiomeric purity of α-amino acids using HPLC analysis of their N-(3,5-dinitrobenzoyl)prolyl derivatives 17 is presented.

ASYMMETRIC ALKYLATIONS OF A SULTAM-DERIVED GLYCINATE EQUIVALENT: PRACTICAL PREPARATION OF ENANTIOMERICALLY PURE α-AMINO ACIDS

Deprotonation/alkylation of sultam-derived N-glycinate equivalent 3 gave crystalline products 5 which on mild hydrolysis furnished α-amino acids 7 (ca.100percent e.e.) in high overall yield.