Water → 1-[3-(2,4-dichlorophenyl)-3-oxo-2-phenylpropyl]-N-[(1,1-dimethylethoxy)carbonyl]-L-histidine

HRID 34489Notes

Reaction equation

HRID 34489 reaction equation
O.[CH3:2][C:3]([CH3:19])([O:5][C:6]([NH:8][C@H:9]([C:16]([OH:18])=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)=[O:7])[CH3:4].[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[C:28](=[O:37])[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[CH2:30]>C(O)C>[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[C:28](=[O:37])[CH:29]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:30][N:13]1[CH:14]=[N:15][C:11]([CH2:10][C@@H:9]([C:16]([OH:18])=[O:17])[NH:8][C:6]([O:5][C:3]([CH3:19])([CH3:2])[CH3:4])=[O:7])=[CH:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 1294381-(2,4-Dichlorophenyl)-2-phenylpropen-1-oneHCID 178454169HCID 178454169, compound

Product 1

HCID 541777141-[3-(2,4-dichlorophenyl)-3-oxo-2-phenylpropyl]-N-[(1,1-dimethylethoxy)carbonyl]-L-histidineYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Water was added to a stirred suspension of N-[(1,1-dimethylethoxy)carbonyl]-L-histidine (13.26 g) in ethanol (100 ml) and 1-(2,4-dichlorophenyl)-2-phenylpropen-1-one (14.5 g) until a clear solution was obtained. The clear solution was allowed to stand for 18 hours, and was then concentrated under reduced pressure to yield a foam which was triturated with hexane. The resulting mixture was filtered to yield 1-[3-(2,4-dichlorophenyl)-3-oxo-2-phenylpropyl]-N-[(1,1-dimethylethoxy)carbonyl]-L-histidine (27.7 g), as a mixture of diastereoisomers.

Workup

  1. customwas obtained
  2. concentrationwas then concentrated under reduced pressure
  3. customto yield a foam which
  4. customwas triturated with hexane
  5. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-55b0f81448e34579be209074caa1e7df
Source dataset
uspto-grants-1988_08
Patent number
US04761483

Reaction notes

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