N-[1-(3-Bromophenyl)-2-hydroxy-1-methylethyl]-2-chloroacetamide → HCID 66931486, compound

HRID 1929460Notes

Reaction equation

HRID 1929460 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:12][C:13](=[O:16])[CH2:14][Cl:15])([CH3:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]([NH:12][C:13](=[O:16])[CH2:14][Cl:15])([CH3:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 58155284N-[1-(3-Bromophenyl)-2-hydroxy-1-methylethyl]-2-chloroacetamide

Product 1

HCID 66931486HCID 66931486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (RS)-N-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide (8.0 g) in dichloromethane was divided in 200 mg aliquots which were separated on chiral HPLC (Reprosil Chiral NR 8 μm, 250×30 mm, Dr. Maisch GmbH) using a 80:20-mixture of heptane and isopropanol as the eluent. The first eluting enantiomer (retention time: 9.40 min), the (S)-(−)-N-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide, was obtained as a viscous, colorless oil (3.30 g, 41% of theory), and the second eluting enantiomer (retention time: 14.14 min), the (R)-(+)-N-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide, was also obtained as a viscous, colorless oil (3.62 g, 45% of theory), with

Workup

  1. customwere separated on chiral HPLC (Reprosil Chiral NR 8 μm, 250×30 mm, Dr. Maisch GmbH)

Sources & evidence

ORD record
ord-7dad7880bcc1422abb377b16c2aab523
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

Loading…