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

HRID 556872
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HRID 556872 반응식
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]
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참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 4409023-Amino-1,2-propanediol, (S)-

생성물 1

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

시약·촉매·용매 1

HCID 21959252Acetonitrile methanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-bdcb195f63e64282909f4dfe884f2e9e
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08058045B2

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