N-[(1R)-2-Hydroxy-1-phenylethyl]acetamide

Base Information

• Chemical Name: N-[(1R)-2-Hydroxy-1-phenylethyl]acetamide
• CAS No.: 78761-26-9
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.219
• Hs Code.: 2924297099
• DSSTox Substance ID: DTXSID70426677
• Nikkaji Number: J51.660K
• Wikidata: Q82239515
• Mol file: 78761-26-9.mol

Synonyms:78761-26-9;Ac-D-phenylglycinol;N-[(1R)-2-Hydroxy-1-phenylethyl]acetamide;N-ACETYL-D-PHENYLGLYCINOL;D(-)-Ac-alpha-phenylglycinol;(R)-N-(2-Hydroxy-1-phenylethyl)acetamide;Ac-D-Phg-ol;D(-)-Ac--phenylglycinol;SCHEMBL8582093;DTXSID70426677;MFCD00038782;AKOS006272900;(r)-(-)-2-acetylamino-2-phenylethanol;BS-24484;CS-0455819;(?)-N-[(R)-alpha-(Hydroxymethyl)benzyl]acetamide;ACETAMIDE,N-[(1R)-2-HYDROXY-1-PHENYLETHYL]-;N-[(1R)-2-Hydroxy-1-phenylethyl]acetamide, AldrichCPR

Chemical Property of N-[(1R)-2-Hydroxy-1-phenylethyl]acetamide

Chemical Property:

• PSA: 49.33000
• LogP: 1.24700
• Storage Temp.: -15°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

98%Min ^*data from raw suppliers

D(-)-Ac-α-phenylglycinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CO)C1=CC=CC=C1
• Isomeric SMILES: CC(=O)N[C@@H](CO)C1=CC=CC=C1
• Uses: Amino acid antagonist. D(-)-Ac-alpha-phenylglycinol

Technology Process of N-[(1R)-2-Hydroxy-1-phenylethyl]acetamide

There total 10 articles about N-[(1R)-2-Hydroxy-1-phenylethyl]acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

D-2-phenylglycinol (56613-80-0) + ethyl acetate (141-78-6) → N-[(1R)-2-hydroxy-1-phenylethyl]acetamide (78761-26-9)

Guidance literature:

With Trimethylacetic acid; at 90 ℃; for 24h; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.02.015

Reference yield: 91.0%

acetic anhydride (108-24-7) + D-(-)-2-amino-2-phenyl-1-ethanol (56613-80-0) → N-[(1R)-2-hydroxy-1-phenylethyl]acetamide (78761-26-9)

Guidance literature:

With triethylamine; In water; at 0 ℃; for 0.5h;

Reference yield: 88.0%

D-2-phenylglycinol (56613-80-0) + acetyl chloride (75-36-5) → N-[(1R)-2-hydroxy-1-phenylethyl]acetamide (78761-26-9)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; at 0 ℃; for 2h;

DOI:10.1016/S0968-0896(02)00381-4

upstream raw materials:

D-(-)-O,N-Diacetyl-α-phenylglycinol

acetic anhydride

D-(-)-2-amino-2-phenyl-1-ethanol

D-2-phenylglycinol

Downstream raw materials:

(R)-2-methyl-4-phenyl-Δ²-oxazoline

Phosphoric acid (R)-2-acetylamino-2-phenyl-ethyl ester dibenzyl ester

(S)-2-acetamido-2-cyclohexylacetic acid

(+)-(2S,1'R)-N-Acetyl-2-(2'-cyclohexenyl)glycin

Refernces

• 1、 Sultane, Prakash R.,Mete, Trimbak B.,Bhat, Ramakrishna G.. "Chemoselective N-deacetylation under mild conditions". supporting information. p. 261 - 264. Retrieved 2014/01/06.
• 2、 Pelagalli, Romina,Chiarotto, Isabella,Feroci, Marta,Vecchio, Stefano. "Isopropenyl acetate, a remarkable, cheap and acylating agent of amines under solvent- and catalyst-free conditions: A systematic investigation". supporting information; experimental part. p. 2251 - 2255. Retrieved 2012/09/08.