Lithium Hydroxide → (S)-2-{4'-[(4-isopropoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid

HRID 29355Notes

Reaction equation

HRID 29355 reaction equation
C[O:2][C:3](=[O:41])[C@@H:4]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]3[O:28][C:29]4[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH:38]([CH3:40])[CH3:39])[C:30]=4[C:31]=3[CH3:32])=[O:26])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH:5]([CH3:7])[CH3:6].[Li+].[OH-]>C1COCC1>[CH:38]([O:37][C:33]1[C:30]2[C:31]([CH3:32])=[C:27]([C:25]([NH:24][C:21]3[CH:20]=[CH:19][C:18]([C:15]4[CH:16]=[CH:17][C:12]([S:9]([NH:8][C@@H:4]([CH:5]([CH3:7])[CH3:6])[C:3]([OH:41])=[O:2])(=[O:10])=[O:11])=[CH:13][CH:14]=4)=[CH:23][CH:22]=3)=[O:26])[O:28][C:29]=2[CH:36]=[CH:35][CH:34]=1)([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68710039(S)-2-{4'-[(4-Isopropoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

Product 1

HCID 59788452(S)-2-{4'-[(4-isopropoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acidYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 370 mg (S)-2-{4′-[(4-isopropoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester dissolved in 2 mL of THF was added 3 mL of LiOH solution (3.6 g LiOH/50 mL MeOH/50 mL H2O). The mixture was stirred at room temperature for 6 days. The solvents were removed under vacuum and the residue was dissolved in 5 mL of water. The solution was acidified and the resulting suspension was filtered. The solid product was dried under vacuum to give 286 mg of (S)-2-{4′-[(4-isopropoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid, obtained as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (dd, J=13.5, 6.7 Hz, 6 H) 1.4 (d, J=6.1 Hz, 6 H) 1.9 (m, 1 H) 2.7 (s, 3 H) 3.5 (t, J=7.2 Hz, 1 H) 4.8 (m, 1 H) 6.9 (d, J=8.6 Hz, 1 H) 7.2 (d, J=8.6 Hz, 1 H) 7.4 (t, J=8.2 Hz, 1 H) 7.8 (d, J=8.8 Hz, 2 H) 7.8 (m, 4 H) 8.0 (m, 3 H) 10.5 (s, 1 H).

Workup

  1. customThe solvents were removed under vacuum
  2. dissolutionthe residue was dissolved in 5 mL of water
  3. filtrationthe resulting suspension was filtered
  4. customThe solid product was dried under vacuum

Sources & evidence

ORD record
ord-69466751915749c7ab0b2a188f1bf4b6
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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