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

HRID 2086247Notes

Reaction equation

HRID 2086247 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f669e1251f8a46a395dea8a33d7df3fc
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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