Esterastin → HCID 100947261, compound

HRID 1395119Notes

Reaction equation

HRID 1395119 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[C:10](=[O:11])[O:9][CH:8]1[CH2:12][CH:13]([O:25][C:26]([CH:28]([NH:33][C:34]([CH3:36])=[O:35])[CH2:29][C:30]([NH2:32])=[O:31])=[O:27])[CH2:14][CH:15]=[CH:16][CH2:17][CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[H][H]>[Pt]=O.CO>[CH3:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]([O:25][C:26]([C@@H:28]([NH:33][C:34]([CH3:36])=[O:35])[CH2:29][C:30]([NH2:32])=[O:31])=[O:27])[CH2:12][C@@H:8]1[O:9][C:10](=[O:11])[C@H:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 2

HCID 125669Esterastin2×HCID 178418361HCID 178418361, compound

Product 1

HCID 100947261HCID 100947261, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Esterastin (95 mg) was taken up into 10 ml of methanol, and this methanolic solution of esterastin was admixed with 20 mg of platinum oxide as the hydrogenation catalyst. The mixture was subjected to hydrogenation with hydrogen gas at 20 lbs. per square inch at ambient temperature for 2 hours. After the reduction was completed, the reaction mixture was filtered to remove the platinum oxide. The filtrate (the reaction solution) was concentrated to dryness to yield 96 mg of a colorless powder of tetrahydroesterastin which gave a single spot in a silica gel thin layer chromatography.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove the platinum oxide
  3. concentrationThe filtrate (the reaction solution) was concentrated to dryness

Sources & evidence

ORD record
ord-ca88eb6465774dc7841476d55e8f949a
Source dataset
uspto-grants-1980_05
Patent number
US04202824

Reaction notes

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