Lithium Hydroxide → HCID 59263287, compound

HRID 643996Notes

Reaction equation

HRID 643996 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:33])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:32])[NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:18][CH:17]=1)(=[O:15])=[O:14]>C1COCC1>[CH2:24]([NH:23][C:22]([C:19]1[CH:20]=[CH:21][C:16]([S:13]([NH:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]([OH:33])=[O:4])(=[O:14])=[O:15])=[CH:17][CH:18]=1)=[O:32])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68579559HCID 68579559, compound

Product 1

HCID 59263287HCID 59263287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1 N aqueous lithium hydroxide (0.78 mL) is added to a solution of the title B compound, 2-(4-phenethylcarbamoyl-benzenesulfonylamino)-benzoic acid methyl ester (113.8 mg, 0.259 mmol) in 4 mL of THF. The reaction is stirred overnight at RT. The solvent is evaporated under a stream of nitrogen, and the residue is partitioned between water (6 mL) and EtOAc. The aqueous layer is washed with EtOAc (1 mL) and then acidified by adding it to a stirred solution of 1 N aqueous HCl (25 mL) to form a white solid. The solid is collected by filtration, washed with water, and dried under vacuum to give 2-(4-phenethylcarbamoyl-benzenesulfonylamino)-benzoic acid: m.p. 242-244° C.; ESI-MS 439.04 [M+1]+.

Workup

  1. customThe solvent is evaporated under a stream of nitrogen
  2. customthe residue is partitioned between water (6 mL) and EtOAc
  3. washThe aqueous layer is washed with EtOAc (1 mL)
  4. additionby adding it to a stirred solution of 1 N aqueous HCl (25 mL)
  5. customto form a white solid
  6. filtrationThe solid is collected by filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-851569359a6b4846a102f25b45afb227
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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