HCID 15860250, compound → HCID 10624435, compound

HRID 1417936Notes

Reaction equation

HRID 1417936 reaction equation
[S:1]([O:5][C:6]1[CH:23]=[CH:22][C:21]2[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15]([C:24](=[O:33])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:14][CH2:13]4)[CH2:10][CH2:9][C:8]=2[CH:7]=1)(=[O:4])(=[O:3])[NH2:2]>CCOC(C)=O.C(O)C.[Pt](=O)=O>[S:1]([O:5][C:6]1[CH:23]=[CH:22][C:21]2[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C@@H:15]([C:24](=[O:33])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]=2[CH:7]=1)(=[O:4])(=[O:3])[NH2:2]

Participants

5

Reactant 1

HCID 15860250HCID 15860250, compound

Product 1

HCID 10624435HCID 10624435, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution comprising about 210 mg of compound 5a (m=6) in about 6 ml of EtOAc and about 2 ml of ethanol (EtOH, 2 ml) was stirred over about 40 mg of platinum (IV) oxide (PtO2) under an atmosphere of hydrogen for 2.5 h. The catalyst was removed by filtration and the filtrate concentrated. The residue was purified by silica gel chromatography (Petroleum ether: EtOAc, 1:1), yielding pure compound 6a (201 mg, 95.3%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by silica gel chromatography (Petroleum ether: EtOAc, 1:1)

Sources & evidence

ORD record
ord-8fbd13cbfadd41c8bd23bd96ab02929b
Source dataset
uspto-grants-1999_03
Patent number
US05880115

Reaction notes

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