Benzyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrole-2-carboxylate → 5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrole-2-carboxylic acid

HRID 1964672Notes

Reaction equation

HRID 1964672 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:38])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]([O:30]CC3C=CC=CC=3)=[O:29])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:11]=1>C(O)C.[C].[Pd]>[CH3:1][O:2][CH2:3][C@H:4]([CH3:38])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]([OH:30])=[O:29])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][Si:13]([CH:17]([CH3:19])[CH3:18])([CH:20]([CH3:21])[CH3:22])[CH:14]([CH3:15])[CH3:16])[CH:11]=1

Participants

4

Reactant 1

HCID 66680782Benzyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrole-2-carboxylate

Product 1

HCID 666835375-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrole-2-carboxylic acidYield 95.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Benzyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrole-2-carboxylate (34.40 g, 64.0 mmol) synthesized in Example (106b) was dissolved in ethanol (320 mL), and a 10% palladium carbon catalyst (3.54 g) was added, followed by stirring for 2 hours under hydrogen atmosphere. The palladium carbon catalyst was removed by Celite filtration, and the solvent was distilled off under reduced pressure to afford the desired compound (27.31 g, yield 95%) as a white solid.

Workup

  1. customThe palladium carbon catalyst was removed by Celite filtration
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-936aab46ff28424b89c449acbe54cf67
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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