158807-51-3

Basic information

• Product Name: METHYL (R)-N-BOC-3-PHENYL-BETA-ALANINATE
• Synonyms: METHYL (R)-N-BOC-3-PHENYL-BETA-ALANINATE ;(R)-3-tert-Butoxycarbonylamino-3-phenyl-propionic acid methyl ester;(R)-Methyl 4-(tert-butoxycarbonylamino)-3-phenylbutanoate
• CAS NO: 158807-51-3
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33154
• Mol File: 158807-51-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 398.7°Cat760mmHg
• Flash Point: 195°C
• Appearance: /
• Density: 1.098g/cm³
• Vapor Pressure: 1.44E-06mmHg at 25°C
• Refractive Index: 1.504
• CAS DataBase Reference: METHYL (R)-N-BOC-3-PHENYL-BETA-ALANINATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (R)-N-BOC-3-PHENYL-BETA-ALANINATE(158807-51-3)
• EPA Substance Registry System: METHYL (R)-N-BOC-3-PHENYL-BETA-ALANINATE(158807-51-3)

Safety Data

• Hazardous Substances Data: 158807-51-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H21NO4/c1-15(2,3)20-14(18)16-12(10-13(17)19-4)11-8-6-5-7-9-11/h5-9,12H,10H2,1-4H3,(H,16,18)/t12-/m1/s1

Upstream product

• 909804-54-2 2-(tert-butoxycarbonylamino-phenyl-methyl)-malonic acid dimethyl ester 
• 100-42-5 styrene 
• 67-56-1 methanol 
• 5661-55-2 4-phenylazetidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-52-7 benzaldehyde 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 1426822-85-6 C₁₆H₂₀F₃NO₄ 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 158009-86-0 (S_S,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate 
• 4248-19-5 tert-butyl carbazate 
• 265669-72-5 tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate 
• 602275-66-1 (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-phenyl-propionic acid methyl ester 

Downstream Products

• 908290-58-4 (R)-2-methyl-4-[N-(tert-butoxycarbonyl)amino]-4-phenylbutan-2-ol 
• 3466-80-6 (R)-(+)-6-phenylpiperidine 
• 212560-70-8 (+)-(6R)-6-phenylpiperidin-2-one 
• 212560-69-5 (R)-5-Amino-5-phenyl-pentanoic acid ethyl ester 
• 212560-68-4 (R)-ethyl 5-[(tert-butoxycarbonyl)amino]-5-phenylpentanoate 
• 1236280-73-1 methyl (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-fluoro-3-phenylpropanoate 
• 212560-65-1 (R)-tert-butyl (3-oxo-1-phenylpropyl)carbamate 
• 37088-67-8 methyl (3R)-3-amino-3-phenylpropanoate 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 158830-39-8 methyl (2S,3S)-2-hydroxy-3-(N-tert-butoxycarbonylamino)-3-phenylpropanoate 

Relevant articles and documents

Studies on N-activation for the lipase-catalyzed enantioselective preparation of β-amino esters from 4-phenylazetidin-2-one

The effect of N-substitution was examined for the enantio-selective lipase-catalyzed ring-opening reaction of racemic 4-phenylazetidin-2-one with methanol in dry organic solvents. Marked differences in the reactivity of various N-protected 4-phenylazetidin-2-ones were observed. Preparativescale reactions with Candida antarctica lipase B (Novozym 435 preparation) yielded N-acylated methyl (R)-3-amino-3- phenylpropanoates with enantiomeric excess (ee) values >99% in up to a 49% isolated yield, whereas Thermomyces lanuginosus lipase (Lipozyme TM IM) gave enantiomerically enriched methyl (S)-3-acetamido-3-phenylpropanoate. Candida antarctica lipase A catalyzed the cleavage of the N-chloroacetyl protective group, whereas all of the other examined lipases underwent the ring-opening reaction.

Disulfonimide-catalyzed asymmetric synthesis of β3-amino esters directly from N-Boc-amino sulfones

An asymmetric Mannich reaction of silyl ketene acetals with N-Boc-amino sulfones has been developed. A chiral disulfonimide efficiently catalyzes both the in situ generation of the corresponding N-Boc imines and the asymmetric Mannich reaction with excellent yields and enantioselectivities. Kinetic studies confirm a proposed stepwise mechanism.

Fluorinated β2- and β3-amino acids: Synthesis and inhibition of α-chymotrypsin

The synthesis of a series of -fluorinated β2- and β3-amino acid derivatives is described. Stereoselective fluorination at the -carbon of the β3-amino acids was achieved by deprotonation with lithium diisopropylamide followed by treatment with N-fluorobenzenesulfonimide. Fluorination of β2-amino acids employed the chiral auxiliary (4R)-4-benzyl-2-oxazolidinone. The α-fluorinated amino acids and their non-fluorinated precursors were found to competitively inhibit α-chymotrypsin. Georg Thieme Verlag Stuttgart New York.