3-Benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester → 4-((S)-2-tert-Butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-3-hydroxy-benzoic acid methyl ester

HRID 1814378Notes

Reaction equation

HRID 1814378 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:25])(=[O:24])[NH:11][C@H:12]([C:21](=[O:23])[NH2:22])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([O:26]CC2C=CC=CC=2)[CH:5]=1>CCO.[Pd]>[CH3:1][O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:24])(=[O:25])[NH:11][C@H:12]([C:21](=[O:23])[NH2:22])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([OH:26])[CH:5]=1

Participants

4

Reactant 1

HCID 697302973-Benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester

Product 1

HCID 697313854-((S)-2-tert-Butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-3-hydroxy-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester (7.40 g, 15.0 mmol) in EtOH (100 mL) was shaken with 20% Pd/C (1.0 g) under H2 (50 psi) for 1.5 h using a Parr apparatus. The reaction mixture was filtered through celite and concentrated. 4-((S)-2-tert-Butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-3-hydroxy-benzoic acid methyl ester was obtained (6.03 g, 99%) as an off white foam. MS m/z 401.2 (M−1).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2383aa64c2bb420f893514737d3c7129
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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