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

HRID 2086247ノート

反応式

HRID 2086247 の反応式
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

参加物

5

反応物 3

HCID 7751Ethyl chloroacetate2 回HCID 8471Triethylamine2 回HCID 69545687Methyl 3-amino-2-([(benzyloxy)carbonyl]amino]propanoate trifluoroacetate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f669e1251f8a46a395dea8a33d7df3fc
出典データセット
uspto-grants-2004_04
特許番号
US06723722B1

反応ノート

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