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Hydrochloric Acid → 3-Hydroxy-4-(3-(4-pentylphenylsulfonamido)propanamido)benzoic acid

HRID 493156
Notes
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Reaction equation

HRID 493156 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=O)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[NH2:31])[C:25]([OH:27])=[O:26].Cl>CN(C=O)C>[OH:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[NH:31][C:18](=[O:20])[CH2:17][CH2:16][NH:15][S:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH:10]=1)(=[O:13])=[O:14])[C:25]([OH:27])=[O:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1375664-Amino-3-hydroxybenzoic acidHCID 690579943-(4-Pentylphenylsulfonamido)propanoic acid

Product 1

HCID 690603703-Hydroxy-4-(3-(4-pentylphenylsulfonamido)propanamido)benzoic acidYield 115.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of the product of Step 1 (200 mg, 0.67 mmol) in dry DMF (7 mL) was added 1,1-carbonyldiimidazole (CDI) (120 mg, 0.73 mmol). The resulting mixture was stirred at 40° C. for 1 h, then treated with 3-hydroxy-4-aminobenzoic acid (107 mg, 0.7 mmol). The mixture was stirred at 40° C. for 16 h, then poured into 1N aqueous HCl (100 mL). The resulting yellow precipitate was filtered, washed with diethyl ether, and azeotroped to dryness once from toluene to give the crude title compound (337 mg), which was used directly in the next step without further purification. MS m/e 434.

Workup

  1. stirringThe mixture was stirred at 40° C. for 16 h
  2. filtrationThe resulting yellow precipitate was filtered
  3. washwashed with diethyl ether
  4. customazeotroped to dryness once from toluene

Sources & evidence

ORD record
ord-16de4f4ea1b24ad0b6cfa4c873dd583d
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07534804B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes