HCID 69280781, compound → HCID 86701106, compound

HRID 1396249Notes

Reaction equation

HRID 1396249 reaction equation
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][O:8][C@@H:9]2[C@@H:17]([CH:18]=[CH2:19])[O:16][C@H:15]3[C@H:11]([N:12]=[C:13]([N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[S:14]3)[C@H:10]2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[CH:5][CH:4]=1>[Ni].C(O)C>[CH2:18]([C@H:17]1[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:24])[CH3:25])[S:14]2)[CH:10]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C@@H:9]1[O:8][CH2:7][C:6]1[CH:39]=[CH:40][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:19]

Participants

4

Reactant 1

HCID 69280781HCID 69280781, compound

Product 1

HCID 86701106HCID 86701106, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of above crude compound 45 (220 mg, purity 50%) was dissolved into ethanol (15 mL) and treated with Ranney Ni (100 mg) under H2 atmosphere overnight at room temperature. After filtration, the organic solution was concentrated to give crude compound 46 (200 mg, purity 48% by LC-MS), which was used in the next step without further purification. (ES, m/z): [M+H]+ 573.0.

Workup

  1. filtrationAfter filtration
  2. concentrationthe organic solution was concentrated

Sources & evidence

ORD record
ord-602f411952ff470e970282097453e753
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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