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

HRID 493156Notes

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]

Participants

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

stirringThe mixture was stirred at 40° C. for 16 h
filtrationThe resulting yellow precipitate was filtered
washwashed with diethyl ether
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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