HCID 86752822, compound → HCID 67701182, compound

HRID 964624Notes

Reaction equation

HRID 964624 reaction equation
[CH3:1][C:2]([Si:5]([CH3:42])([CH3:41])[O:6][CH:7]([C:22]1[CH:27]=[CH:26][C:25]([O:28]CC2C=CC=CC=2)=[C:24]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:23]=1)[CH2:8][NH:9][C@@H:10]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12])([CH3:4])[CH3:3]>CO.[Pd]>[CH3:4][C:2]([Si:5]([CH3:41])([CH3:42])[O:6][CH:7]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([NH:36][S:37]([CH3:40])(=[O:38])=[O:39])[CH:23]=1)[CH2:8][NH:9][C@@H:10]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:11]([OH:13])=[O:12])([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 86752822HCID 86752822, compound

Product 1

HCID 67701182HCID 67701182, compoundYield 111.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxy-benzeneacetic acid (4.04 g, 6.5 mmol) in MeOH (50 mL) containing 0.42 g of 10% Pd/C was sparged with H2 at 20° C. By TLC (10% MeOH/CH2Cl2), the reaction was complete after 40 minutes whereupon the reaction mixture was filtered and concentrated in vacuo to obtain 3.8 g of the title compound as a solid foam.

Workup

  1. customwas sparged with H2 at 20° C
  2. filtrationwas filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b75d282605fe433f908d99ef860b0d44
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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