Dichloromethane → N-[2-(4-benzyloxy-phenyl)-2-hydroxy-ethyl]-2-chloro-acetamide

HRID 588223Notes

Reaction equation

HRID 588223 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[OH:4].CCN(CC)CC.C(Cl)Cl.[Cl:29][CH2:30][C:31](Cl)=[O:32]>CO>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([OH:4])[CH2:2][NH:1][C:31](=[O:32])[CH2:30][Cl:29])=[CH:6][CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 4239902-Amino-1-(4-benzyloxyphenyl)ethanol

Product 1

HCID 66653971N-[2-(4-benzyloxy-phenyl)-2-hydroxy-ethyl]-2-chloro-acetamideYield 66.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-amino-1-(4-benzyloxy-phenyl)-ethanol (20.10 g; 82.6 mmol), Et3N (13.82 mL; 99.1 mmol), CH2Cl2 (200 mL) and MeOH (20 mL) was added dropwise chloroacetyl chloride (7.24 mL; 90.9 mmol) at −10° C. The resulting mixture was allowed to warm to RT and stirred overnight, and subsequently concentrated in vacuo. The residue was purified by flash chromatography (SiO2, EtOAc) to afford N-[2-(4-benzyloxy-phenyl)-2-hydroxy-ethyl]-2-chloro-acetamide (17.45 g).

Workup

  1. concentrationsubsequently concentrated in vacuo
  2. customThe residue was purified by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-0d4cae44792543b9b2a8901ef4b0f967
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

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