Lithium hydroxide, monohydrate → 2-[(4-Benzofuran-2-yl-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid

HRID 2179928Notes

Reaction equation

HRID 2179928 reaction equation
C[O:2][C:3](=[O:43])[CH:4]([N:12]([CH:27]([C:34]1[O:42][C:38]2=[CH:39][CH:40]=[CH:41][C:37]2=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[C:18]([CH3:25])[C:17]=1[CH3:26])(=[O:15])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O[Li].O>C1COCC1.CO.O>[O:42]1[C:38]2=[CH:39][CH:40]=[CH:41][C:37]2=[CH:36][CH:35]=[C:34]1[CH:27]([N:12]([S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[C:18]([CH3:25])[C:17]=1[CH3:26])(=[O:14])=[O:15])[CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:43])=[O:2])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 865904242-[(4-Benzofuran-2-yl-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester

Product 1

HCID 865904252-[(4-Benzofuran-2-yl-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

2-[(4-Benzofuran-2-yl-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester (40 mg, 0.067 mmol) was taken in a mixture of THF:MeOH:H2O (3:2:1) and then added 1N aqueous solution of LiOH.H2O (0.40 mL, 0.40 mmol). The reaction mixture was stirred at room temperature for 12 h. Solvents were removed and the residue was partitioned between water and ethyl acetate. The aqueous layer was acidified using 10% KHSO4 solution. The organic layer was separated, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate and methanol (9:1) to obtain 2-[(4-Benzofuran-2-yl-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid. (29 mg, 75%) as a white solid. 1H NMR (CDCl3, 400 MHz): δ7.59 (d, 2H), 7.48 (d, 2H), 7.42 (d, 2H), 7.19 (m, 4H), 7.06, 6.88 (2m, 6H), 6.37 (s, 1H), 4.55 (m, 3H), 3.70 (s, 3H), 3.19, 2.85 (2m, 2H), 2.56, 2.00, 1.98 (3s, 9H). ESI− (M−H): 582.

Workup

  1. customSolvents were removed
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-36e0bf70ad24428db06f0e597cbe7fd1
Source dataset
uspto-grants-2005_05
Patent number
US06887877B2

Reaction notes

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