Hydrochloric Acid → 3-Benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethyoxy-ethylsulfamoyl-)benzoic acid

HRID 1814358Notes

Reaction equation

HRID 1814358 reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:29])(=[O:28])[NH:11][CH:12]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])=[C:6]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:5]=1.[OH-].[Li+].Cl>C(OCC)(=O)C>[CH2:31]([O:30][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[S:10](=[O:28])(=[O:29])[NH:11][CH:12]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[C:3]([OH:38])=[O:2])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 697315433-Benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethoxy-ethylsulfamoyl)-benzoic acid methyl ester

Product 1

HCID 1317248233-Benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethyoxy-ethylsulfamoyl-)benzoic acidYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethoxy-ethylsulfamoyl)-benzoic acid methyl ester (6.82 g, 12.4 mmol) was combined and stirred with 1M lithium hydroxide (26 mL, 26 mmol) in tetrohydrofuran (250 mL) at room temperature overnight. The reaction mixture was diluted with ethyl acetate and acidified with 1M HCl (26 mL). The organic layer was collected and extracted with water, brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 3-benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethyoxy-ethylsulfamoyl-)benzoic acid (4.32 g, 8.0 mmol, 65%). MS (APCI) m/z 536.3 (M−1).

Workup

  1. customThe organic layer was collected
  2. extractionextracted with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2824492aa2a4b70be01d1cda49bc815
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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