(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide → HCID 86756959, compound

HRID 1979247Notes

Reaction equation

HRID 1979247 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([NH:24][NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]>C(O)(=O)C.[Pt]=O>[CH:15]1([CH2:14][CH2:13][CH2:12][C@@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([NH:24][NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[C:9](=[O:10])[NH:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 1

HCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86756959HCID 86756959, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1.0 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbarnoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 30 ml of glacial acetic acid was hydrogenated in the presence of 0.300 g of platinum(II)oxide for 2 hours. The catalyst was removed by filtration and the solvent was evaporated and trituration with hexane gave 0.94 g of 2(R)-[4-cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]butyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-249ea1ec86b44febba36d840e54cd4ef
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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