Hydrochloric Acid → HCID 59263297, compound

HRID 644002Notes

Reaction equation

HRID 644002 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:32])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=2)=[CH:16][CH:15]=1)(=[O:13])=[O:12].[OH-].[Li+].Cl>C1COCC1>[CH2:30]([O:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([S:11]([NH:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:33])=[O:2])(=[O:13])=[O:12])=[CH:15][CH:16]=2)=[O:32])=[CH:28][CH:27]=1)[CH3:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68579485HCID 68579485, compound

Product 1

HCID 59263297HCID 59263297, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title D compound, 2-{4-[2-(4-ethoxy-phenyl)-acetylamino]-benzenesulfonyl-amino}-benzoic acid methyl ester (189.1 mg, 0.356 mmol) is dissolved in 4 mL of THF and 1.07 mL of 1 N aqueous lithium hydroxide is added. The mixture is stirred at RT for 3 days and is then concentrated under a stream of nitrogen. The residue is taken up in warm water (20 mL) to give a clear solution. The solution is added slowly to 30 mL of 1 N aqueous HCl. The resulting precipitate is collected by filtration, washed with water, and dried under vacuum to give 2-{4-[2-(4-ethoxy-phenyl)-acetylamino]benzenesulfonylamino}benzoic acid: m.p. 241-242° C.: ESI-MS 455 [M+1]+.

Workup

  1. concentrationis then concentrated under a stream of nitrogen
  2. customto give a clear solution
  3. filtrationThe resulting precipitate is collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-55ea78f4fdd347b2b7be2825b73b7504
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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