Chloroacetyl chloride → 2-Chloro-N-[(2R)-2,3-dihydroxypropyl]acetamide

HRID 556877Notes

Reaction equation

HRID 556877 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][C@@H:10]([OH:13])[CH2:11][OH:12].[Cl:14][CH2:15][C:16](Cl)=[O:17]>CC#N.CO>[Cl:14][CH2:15][C:16]([NH:8][CH2:9][C@@H:10]([OH:13])[CH2:11][OH:12])=[O:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 6994409(2R)-3-aminopropane-1,2-diol

Product 1

HCID 596135412-Chloro-N-[(2R)-2,3-dihydroxypropyl]acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

Triethylamine (1.83 mL, 13.2 mmol) was added to a solution of (R)-3-amino-1,2-propanediol (1.00 g, 11.0 mmol) in a mixture CH3CN/MeOH (36 mL/16 mL) at −10° C. under nitrogen. Chloroacetyl chloride (0.98 ml, 12.0 mmol) was added dropwise at −10° C. over 30 min. The reaction mixture was allowed to reach room temperature and stirred for 16 h. The mixture was concentrated and purified by flash column chromatography on silica gel, eluting with methanol/ethyl acetate (8/92), to give the title compound as a white solid (1.43 g, 78%).

Workup

  1. customto reach room temperature
  2. concentrationThe mixture was concentrated
  3. custompurified by flash column chromatography on silica gel
  4. washeluting with methanol/ethyl acetate (8/92)

Sources & evidence

ORD record
ord-136995a266624269b162ea3b37111367
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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