3-Hydroxy-4-(3-(4-pentylphenylsulfonamido)propanamido)benzoic acid → 2-(2-(4-Pentylphenylsulfonamido)ethyl)benzo[d] oxazole-6-carboxylic acid

HRID 493157Notes

Reaction equation

HRID 493157 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][C:12](=[O:30])[CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:5]([OH:7])=[O:6]>C(O)(=O)C>[CH2:25]([C:22]1[CH:21]=[CH:20][C:19]([S:16]([NH:15][CH2:14][CH2:13][C:12]2[O:30][C:9]3[CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=[CH:2][C:10]=3[N:11]=2)(=[O:18])=[O:17])=[CH:24][CH:23]=1)[CH2:26][CH2:27][CH2:28][CH3:29]

Participants

3

Reactant 1

HCID 690603703-Hydroxy-4-(3-(4-pentylphenylsulfonamido)propanamido)benzoic acid

Product 1

HCID 690578142-(2-(4-Pentylphenylsulfonamido)ethyl)benzo[d] oxazole-6-carboxylic acidYield 9.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Step 2 (337 mg, 1.29 mmol) in glacial acetic acid (4 mL) in a sealed tube was heated at 120° C. for 60 h. The solvent was evaporated under reduced pressure, and the resulting residue purified by preparative HPLC to give the product (52 mg). MS m/e 417; HPLC retention time 3.44 min.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue purified by preparative HPLC

Sources & evidence

ORD record
ord-88dac9840231400b849fd7f21f349ff0
Source dataset
uspto-grants-2009_05
Patent number
US07534804B2

Reaction notes

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