3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(1-ethyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide → HCID 59346863, compound

HRID 20526Notes

Reaction equation

HRID 20526 reaction equation
[CH3:1][C:2]([Si:5]([CH3:36])([CH3:35])[O:6][CH2:7][C@@H:8]([O:10][C:11]1[CH:12]=[C:13]([CH:24]=[C:25]([O:27]CC2C=CC=CC=2)[CH:26]=1)[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=1)=[O:15])[CH3:9])([CH3:4])[CH3:3]>C1COCC1>[CH3:1][C:2]([Si:5]([CH3:36])([CH3:35])[O:6][CH2:7][C@@H:8]([O:10][C:11]1[CH:12]=[C:13]([CH:24]=[C:25]([OH:27])[CH:26]=1)[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=1)=[O:15])[CH3:9])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 593469163-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(1-ethyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide

Product 1

HCID 59346863HCID 59346863, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(1-ethyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide (2.40 g, 4.71 mmol) and THF (80 mL) was evacuated and purged with Argon (×3). Palladium on carbon (10%, 422 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 (1.87 g, 95%).

Workup

  1. custompurged with Argon (×3)
  2. additionPalladium on carbon (10%, 422 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-6f4de721af3743d58a7254e9affa6dba
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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