Chloroacetyl chloride → (S)-2-Chloro-N-(2,3-dihydroxypropyl)acetamide

HRID 384712Notes

Reaction equation

HRID 384712 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 4409023-Amino-1,2-propanediol, (S)-

Product 1

HCID 11378718(S)-2-Chloro-N-(2,3-dihydroxypropyl)acetamideYield 90%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

Triethylamine (4.0 ml, 28.9 mmol) was added to a solution of (S)-3-amino-1,2-propanediol (2.2 g, 24.1 mmol) in a mixture of CH3CN/MeOH (80 mL/13 mL) at −10° C. under nitrogen. Chloroacetyl chloride (2.1 mL, 26.5 mmol) was then 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 under vacuum 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 (3.63 g, 90%).

Workup

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

Sources & evidence

ORD record
ord-7633edc5b3cc499ea9280941b6a17ffb
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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