Citric Acid → 3-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acid

HRID 1814330Notes

Reaction equation

HRID 1814330 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:28])(=[O:27])[NH:11][C@H:12]([C:21](=[O:26])[N:22]([O:24][CH3:25])[CH3:23])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:5]=1.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(OCC)(=O)C>[CH2:30]([O:29][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[S:10](=[O:27])(=[O:28])[NH:11][C@H:12]([C:21](=[O:26])[N:22]([O:24][CH3:25])[CH3:23])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:3]([OH:37])=[O:2])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 865882233-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acid methyl ester

Product 1

HCID 865882253-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acid methyl ester (8.20 g, 15.3 mmol) in tetrahydrofuran (150 mL) at room temperature was added 1N lithium hydroxide (30.5 mL, 15.3 mmol). The reaction was stirred at room temperature for 3.5 h. The reaction was then diluted with ethyl acetate (300 mL) and acidified to pH 2 with 5% citric acid. The organic layer was then washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield 3-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acid as a white foam (2.9 g, 100%). MS(ACI) m/z 521.1 (M−H).

Workup

  1. washThe organic layer was then washed with saturated sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b6b0ff0563b44e729d774e613b5896b3
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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