Piperidine → (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2'-glycinyl-4-methylvalerohydrazide

HRID 651779Notes

Reaction equation

HRID 651779 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:19]([NH:21][NH:22][C:23](=[O:43])[CH2:24][NH:25]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>ClCCl>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:19]([NH:21][NH:22][C:23](=[O:43])[CH2:24][NH2:25])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86757289(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2'-[N-(9-fluorenylmethyloxycarbonyl)-glycinyl]-4-methylvalerohydrazide

Product 1

HCID 86757290(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2'-glycinyl-4-methylvalerohydrazideYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.54 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2′-[N-(9-fluorenylmethyloxycarbonyl)-glycinyl]-4-methylvalerohydrazide in 20 ml of dichloromethane was treated with 1.0 ml of piperidine. The mixture was stirred for 1.5 hours at room temperature and evaporated. The residue was purified by flash column chromatography on silica gel using methanol/dichloromethane (1:9) for the elution to give 0.83 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2′-glycinyl-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. customevaporated
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washfor the elution

Sources & evidence

ORD record
ord-f174da8a0c5f4404be63216121d68639
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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