2'-isobutyl-2'-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide → 2'-Isobutyl-4-methylvalerohydrazide

HRID 1979206Notes

Reaction equation

HRID 1979206 reaction equation
[CH2:1]([N:5](C(=O)[C@@H](C)NC(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[NH:6][C:7](=[O:13])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:2]([CH3:4])[CH3:3]>ClCCl.N1CCCCC1>[CH2:1]([NH:5][NH:6][C:7](=[O:13])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 1317225872'-isobutyl-2'-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide

Product 1

HCID 179023992'-Isobutyl-4-methylvalerohydrazide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8082PiperidineSolvent

Procedure

A solution of 1.67 g of (E)-2(R)-[1(S)-(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethoxycarbonyl)-D-alanyl]-4-methylvalerohydrazide in a mixture of 20 ml of dichloromethane and 5 ml of piperidine was stirred at room temperature for 2 hours. The solution was evaporated and the residue was triturated with hexane/diethyl ether (2:1). The residue was purified by flash column chromatography on silica gel using methanol/dichloromethane (5:95) for the elution to give 0.75 g of (E)-2′-(D-alanyl)-2(R)-[1(S)-(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a white foam.

Workup

  1. customThe solution was evaporated
  2. customthe residue was triturated with hexane/diethyl ether (2:1)
  3. customThe residue was purified by flash column chromatography on silica gel
  4. washfor the elution

Sources & evidence

ORD record
ord-7088ee8e3005457880334fbf7d6ac5a7
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

Loading…