Ethyl chloroacetate → Methyl 2-[[(benzyloxy)carbonyl]amino]-3-((2-ethoxy-2-oxoethyl)amino]propanoate

HRID 2086247노트

반응식

HRID 2086247 반응식
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH:10]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:11]([O:13][CH3:14])=[O:12].C(N(CC)CC)C.Cl[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C)C=O>[CH2:19]([O:18][C:16]([NH:15][CH:10]([CH2:9][NH:8][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:11]([O:13][CH3:14])=[O:12])=[O:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 7751Ethyl chloroacetate2회HCID 8471Triethylamine2회HCID 69545687Methyl 3-amino-2-([(benzyloxy)carbonyl]amino]propanoate trifluoroacetate

생성물 1

HCID 22727040Methyl 2-[[(benzyloxy)carbonyl]amino]-3-((2-ethoxy-2-oxoethyl)amino]propanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

A mixture of methyl 3-amino-2-([(benzyloxy)carbonyl]amino]propanoate trifluoroacetate (8.9 g) and triethylamine (30.6 ml) in dimethylformamide (89 ml) was treated by a slow dropwise addition of a solution of ethyl chloroacetate (7.8 ml) in dimethylformamide (20 ml). After stirring at room temperature for 12 hours, triethylamine (20.4 ml) was added again, and the mixture was treated by a slow dropwise addition of a solution of ethyl chloroacetate (5.2 ml) in dimethylformamide (15 ml) and stirred at room temperature for further 6 hours. The system was partitioned between water and ethyl acetate and the organic phase was washed with saturated brine, dried (MgSO2) and concentrated under reduced pressure. The residue was purified by a column chromatography on a silica gel (hexane:ethyl acetate=1:4) to obtain methyl 2-[[(benzyloxy)carbonyl]amino]-3-((2-ethoxy-2-oxoethyl)amino]propanoate (6.6 g) as a colorless oil.

후처리

  1. stirringstirred at room temperature for further 6 hours
  2. customThe system was partitioned between water and ethyl acetate
  3. washthe organic phase was washed with saturated brine
  4. dry with materialdried (MgSO2)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a column chromatography on a silica gel (hexane:ethyl acetate=1:4)

출처 및 근거

ORD 기록
ord-f669e1251f8a46a395dea8a33d7df3fc
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06723722B1

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