HCID 86756878, compound → (E)-2'-[(1-amino-1-cyclopentyl)carbonyl]-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

HRID 1979192Notes

Reaction equation

HRID 1979192 reaction equation
C1C2C(COC([NH:18][C:19]3([C:24]([N:26]([CH2:55][CH:56]([CH3:58])[CH3:57])[NH:27][C:28](=[O:54])[C@@H:29]([C@@H:34]([C:44](=[O:53])[NH:45][O:46][CH:47]4[CH2:52][CH2:51][CH2:50][CH2:49][O:48]4)[CH2:35]/[CH:36]=[CH:37]/[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]3)=O)C3C(=CC=CC=3)C=2C=CC=1>ClCCl.N1CCCCC1>[NH2:18][C:19]1([C:24]([N:26]([CH2:55][CH:56]([CH3:58])[CH3:57])[NH:27][C:28](=[O:54])[C@@H:29]([C@@H:34]([C:44](=[O:53])[NH:45][O:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)[CH2:35]/[CH:36]=[CH:37]/[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 1

HCID 86756878HCID 86756878, compound

Product 1

HCID 86756877(E)-2'-[(1-amino-1-cyclopentyl)carbonyl]-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazideYield 72.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8082PiperidineSolvent

Procedure

A solution of 0.69 g of (E)-2′-[(1-(9-fluorenylmethyloxycarbonylamino)-1-cyclopentyl)carbonyl]-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in a mixture of 6.4 ml of dichloromethane and 1.6 ml of piperidine was stirred at room temperature for 1 hour. The solution was evaporated and the residue was treated with diethyl ether. The ethereal solution was filtered and evaporated. Chromatography on silica gel using methanol/dichloromethane (1:33) for the elution followed by evaporation gave 0.36 g of (E)-2′-[(1-amino-1-cyclopentyl)carbonyl]-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. additionthe residue was treated with diethyl ether
  3. filtrationThe ethereal solution was filtered
  4. customevaporated
  5. washfor the elution
  6. customfollowed by evaporation

Sources & evidence

ORD record
ord-5d3d4b4e424a4106b0839f50160507b2
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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