Sodium → HCID 86756947, compound

HRID 1979240Notes

Reaction equation

HRID 1979240 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]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:22]([NH:24][N:25]([C:30](=[O:36])[CH2:31][CH2:32][C:33](=[O:35])[CH3:34])[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].[Na]>C(O)C.C(OCC)(=O)C>[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]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:22]([NH:24][N:25]([C:30](=[O:36])[CH2:31][CH2:32][CH:33]([OH:35])[CH3:34])[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]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 86756948HCID 86756948, compound

Product 1

HCID 86756947HCID 86756947, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.160 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-(4-oxovaleryl)-2′-isobutyl-4-methylvalerohydrazide in 10 ml of ethanol was treated with 0.012 g of sodium borobydride. The mixture was stirred for 48 hours and then diluted with ethyl acetate and washed with water and saturated sodium chloride solution. Drying over anhydrous magnesium sulfate and evaporation gave 0.150 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-(4(RS)-hydroxyvaleryl)-2′-isobutyl-4-methylvalerohydrazide in the form of a white foam.

Workup

  1. washwashed with water and saturated sodium chloride solution
  2. dry with materialDrying over anhydrous magnesium sulfate and evaporation

Sources & evidence

ORD record
ord-df9e9fe9009c407c83d98aad1e2979de
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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