Ethyl Acetate → Nalpha-[1(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-Nepsilon-t-butoxycarbonyl-(S)-lysyl-(S)-proline-t-butylester

HRID 4369Notes

Reaction equation

HRID 4369 reaction equation
[C:1]([O:5][C:6](=[O:28])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:27])[C@H:13]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH2:14])([CH3:4])([CH3:3])[CH3:2].[CH2:29]([O:31][C:32](=[O:43])/[CH:33]=[CH:34]/[C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:30].C(OCC)(=O)C>C(OCC)C>[C:1]([O:5][C:6](=[O:28])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:27])[C@H:13]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:14][C@H:33]([C:32]([O:31][CH2:29][CH3:30])=[O:43])[CH2:34][C:35]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:42])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5369605Ethyl (2E)-4-oxo-4-phenyl-2-butenoateHCID 14010669H-Lys(Boc)-Pro-OtBu

Product 1

HCID 86741992Nalpha-[1(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-Nepsilon-t-butoxycarbonyl-(S)-lysyl-(S)-proline-t-butylester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

8.0 g (20 mmoles) of Nε -t-butoxycarbonyl-(S)-lysyl-(S)-proline-t-butylester are dissolved in 100 ml of diethyl ether and 4.48 g (22 mmoles) of E-ethyl-3-benzoyl-acrylate are added to the solution. The reaction mixture is stirred at room temperature for 5 hours. After evaporation of the solvent the title product is isolated on a Kieselgel column in the form of transparent oil. Rf =0.49 i(in a 7:3 eluent mixture of ethyl acetate and ether).

Workup

  1. customAfter evaporation of the solvent the title product
  2. customis isolated on a Kieselgel column in the form of transparent oil

Sources & evidence

ORD record
ord-b8a5aa9b39d74e0b898f76e9233cf62f
Source dataset
uspto-grants-1988_02
Patent number
US04725617

Reaction notes

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