67553-20-2

Basic information

• Product Name: Carbamic acid, (2-hydroxy-1-phenylethyl)-, phenylmethyl ester
• CAS NO: 67553-20-2
• Molecular Formula: C16H17NO3
• Molecular Weight: 271.316
• Mol File: 67553-20-2.mol

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (2-hydroxy-1-phenylethyl)-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (2-hydroxy-1-phenylethyl)-, phenylmethyl ester(67553-20-2)
• EPA Substance Registry System: Carbamic acid, (2-hydroxy-1-phenylethyl)-, phenylmethyl ester(67553-20-2)

Safety Data

• Hazardous Substances Data: 67553-20-2(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 91174-01-5 sodium [(benzyloxy)carbonyl]chloroamide 
• 621-84-1 O-benzyl carbamate 
• 1262306-22-8 benzyloxycarbonylamino-4-chlorobenzoate 
• 3426-71-9 Benzyl N-hydroxycarbamate 
• 204461-11-0 C₁₆H₁₅NO₃ 
• 64420-86-6 O-p-toluenesulfonyl benzyloxyhydroxamate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 96-09-3 styrene oxide 
• 124718-93-0 2-azido-2-phenylethanol 
• 501-53-1 benzyl chloroformate 
• 20989-17-7 Phenylglycinol 
• 100-46-9 benzylamine 
• 101582-03-0 benzylamino-phenyl-acetaldehyde dimethylacetal 

Downstream Products

• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 204461-11-0 C₁₆H₁₅NO₃ 
• 24461-61-8 phenylglycine methyl ester 

Relevant articles and documents

Montmorillonite K10 catalyzed highly regioselective azidolysis of epoxides: A short and efficient synthesis of phenylglycine

A series of β‐hydroxyazides were effectively synthesized from the regioselective ring opening of epoxides by sodium azide using montmorillonite K10 as a novel heterogeneous catalyst in aqueous acetonitrile in good to excellent yields. The utility of this method has been demonstrated by achieving a short synthesis of phenylglycine in 33.5% overall yield.

Osmium-catalyzed vicinal oxyamination of alkenes by N-(4- toluenesulfonyloxy)carbamates

N-(4-Toluenesulfonyloxy)carbamates based on a range of common amine protecting groups serve as preformed nitrogen sources in the intermolecular osmium-catalyzed oxyamination reaction of a variety of mono-, di-, and trisubstituted alkenes. The reactions occur with low catalyst loadings and good yields and afford high regioselectivity for unsymmetrically substituted alkenes.

Resolution and absolute configuration of some a-aminoacetals: En route to enantiopure N-protected a-aminoaldehydes

The first successful resolution of rac-a-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of a-aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N-protection and a new efficient hydrolysis step followed by a reduction of the resulting N-protected a-aminoaldehyde intermediates. A racemization method of optically enriched a-aminoacetals is exemplified to allow valorisation of both enantiomers. Springer-Verlag 2011.

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

Asymmetric aminohydroxylation of substituted styrenes using t-butyl carbamate

A variety of substituted styrenes have been aminohydroxylated using t- butyl carbamate to give either enantiomer of highly enantiomerically enriched N-Boc protected amino alcohols in good yields. Better levels of regioselectivity were observed with (DHQ)2PHAL than with (DHQD)2PH. AL even though the enantioselectivities observed were comparable. One of the amino alcohol products was converted into a novel chiral diamine.