3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-[1-(1-methylethyl)-1H-pyrazol-3-yl]-5-[(phenylmethyl)oxy]benzamide → 3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-[1-(1-methylethyl)-1H-pyrazol-3-yl]benzamide

HRID 20538

Reaction equation

HRID 20538 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:37])[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH:25]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH:20]([CH3:22])[CH3:21])[N:16]=1)=[O:13])C1C=CC=CC=1>C1COCC1>[Si:30]([O:29][CH2:28][C@H:27]([CH3:37])[O:26][C:24]1[CH:23]=[C:11]([CH:10]=[C:9]([OH:8])[CH:25]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH:20]([CH3:21])[CH3:22])[N:16]=1)=[O:13])([C:33]([CH3:35])([CH3:36])[CH3:34])([CH3:32])[CH3:31]

Participants

3

Reactant 1

HCID 536296493-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-[1-(1-methylethyl)-1H-pyrazol-3-yl]-5-[(phenylmethyl)oxy]benzamide

Product 1

HCID 536296483-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-[1-(1-methylethyl)-1H-pyrazol-3-yl]benzamideYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(1-isopropyl-1H-pyrazol-3-yl)benzamide (1.97 g, 3.77 mmol) and THF (70 mL) was evacuated and purged with, Argon (×3). Palladium on carbon (10% w/w, 400 mg) was added and reaction mixture was evacuated and finally purged with hydrogen gas. Reaction mixture was left to stir at ambient temperature under hydrogen for 16 hours. Pd/C was filtered off and concentrated in vacuo to give the product as a colourless oil (1.58 g, 97%).

Workup

  1. custompurged with, Argon (×3)
  2. additionPalladium on carbon (10% w/w, 400 mg) was added
  3. customreaction mixture
  4. customwas evacuated
  5. customfinally purged with hydrogen gas
  6. customReaction mixture
  7. waitwas left
  8. filtrationPd/C was filtered off
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09e532e382744faebd128349e8aaedc0
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Linked notes

Loading…