Sodium Hydroxide → 4-(4-(4-Methylphenylsulfonamido)-3-phenylbutanamido)benzoic acid

HRID 2422944Notes

Reaction equation

HRID 2422944 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:14][C:15]([NH:17][C:18]2[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=2)=[O:16])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH:13]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:14][C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:27][CH:28]=2)=[O:16])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 24786212Ethyl 4-(4-(4-methylphenylsulfonamido)-3-phenylbutanamido)benzoate

Product 1

HCID 247862114-(4-(4-Methylphenylsulfonamido)-3-phenylbutanamido)benzoic acidYield 85.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ester 55 (0.106 g, 0.220 mmol) in methanol (3 ml) and THF (3 ml) was stirred in presence of NaOH (aq, 1M, 1 ml) at room temperature overnight. The solvent was removed under reduced pressure. HCl (aq, 1M, 1.5 ml) was added and the white precipitate was filtered, washed with water (5 ml) and dried under vacuum. Pure 59 was obtained as a white solid (0.085 g, 0.188 mmol, 85%) without further purification, mp 225-227° C. 1H NMR (400 MHz, CD3OD) δ2.39 (3H, s), 2.62 (1H, dd, J 8.4, 14.8 Hz), 2.35 (1H, dd, J 6.6, 14.6 Hz), 3.05 (1H, dd, J 8.0, 13.0 Hz), 3.12 (1H, dd, J 7.2, 12.8 Hz), 7.16-7.19 (3H, m), 7.24-7.27 (2H, m), 7.30 (2H, d, J 7.6 Hz), 7.53 (2H, d, J 8.4 Hz), 7.65 (2H, d, J 8.4 Hz), 7.91 (2H, d, J 9.2 Hz). 13C NMR (100 MHz, DMSO-d3) δ 21.61, 40.65, 42.32, 48.33, 118.95, 125.61, 127.18), 127.26, 128.38, 128.96, 130.02, 130.98, 138.09, 142.47, 143.22, 143.72, 167.55, 170.64. νmax (solid)/(cm−1) 3316, 3277), 1668, 1595, 1531, 1408, 1317, 1254, 1152. MS (API-ES): m/z 451[M−H]− (100%), HRMS (API-ES) m/z found 451.1334 [M−H]−.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionHCl (aq, 1M, 1.5 ml) was added
  3. filtrationthe white precipitate was filtered
  4. washwashed with water (5 ml)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-457bbfdf302448cfa536cece46a7f53b
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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