Methanol → HCID 100947261, compound

HRID 1395118Notes

Reaction equation

HRID 1395118 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].CO.[H][H]>[Pt]=O.[Pd].C(O)C>[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

7

Reactant 3

HCID 887MethanolHCID 125669Esterastin2×HCID 178418361HCID 178418361, compound

Product 1

HCID 100947261HCID 100947261, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

In this process of the second aspect of the invention, the starting esterastin may be dissolved in an organic solvent such as a lower alkanol, for example, methanol or ethanol which is inert to the reaction involved. To this solution is added an amount of a known hydrogenation catalyst such as platinum oxide or palladium metal. The amount of the catalyst may be 2~20% by weight of the starting esterastin. The reduction may carried out in a stream of hydrogen gas or in Parr-apparatus at ambient temperature for a period of time of 2 hours to 12 hours. Usually, it suffices that the catalytic reduction is carried out overnight. After the reaction is completed, the reaction mixture is filtered to remove the catalyst, and the filtrate is concentrated to dryness to afford a crude powder of tetrahydroesterastin.

Workup

  1. customis inert to the reaction involved
  2. filtrationthe reaction mixture is filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-d75ebf78e6f84a5cb55847409865a453
Source dataset
uspto-grants-1980_05
Patent number
US04202824

Reaction notes

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