HCID 12069132, compound → HCID 12069133, compound

HRID 1356204Notes

Reaction equation

HRID 1356204 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C:4]1[CH:9]=[C:8]([CH2:10][C@@H:11]([C:20]([O:22]CC2C=CC=CC=2)=[O:21])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]=[CH:6][C:5]=1[O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33]>CCO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:36])[C:4]1[CH:9]=[C:8]([CH2:10][C@H:11]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:20]([OH:22])=[O:21])[CH:7]=[CH:6][C:5]=1[O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33]

Participants

4

Reactant 1

HCID 12069132HCID 12069132, compound

Product 1

HCID 12069133HCID 12069133, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

5-((2S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-2-methoxycarbonylmethoxy-benzoic acid methyl ester of Step D (135 mg, 0.27 mmol) is stirred in 95% EtOH (3 mL) with Pearlman's catalyst (palladium hydroxide on carbon) (70 mg) and put through a vacuum/purge cycle 3 times with H2 gas. The reaction is then held under 1 atm of H2 overnight. The catalyst is then filtered off on GF/F filter paper and the filtrate concentrated to provide 5-((2S)-2-tert-butoxycarbonylamino-2-carboxy-ethyl)-2-methoxycarbonylmethoxy-benzoic acid methyl ester which is used without further purification.

Workup

  1. customis then held under 1 atm of H2 overnight
  2. filtrationThe catalyst is then filtered off on GF/F
  3. filtrationfilter paper
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-01fd4371f0e44153b1e627da5d37996f
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

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