Lithium Hydroxide → (S)-2-{4'-[(5-acetyl-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid

HRID 29409Notes

Reaction equation

HRID 29409 reaction equation
C[O:2][C:3](=[O:42])[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][C:34]([C:37](=[O:39])[CH3:38])=[C:33]([O:40][CH3:41])[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>[C:37]([C:34]1[CH:35]=[CH:36][C:29]2[O:28][C:27]([C:25]([NH:24][C:21]3[CH:20]=[CH:19][C:18]([C:15]4[CH:14]=[CH:13][C:12]([S:9]([NH:8][C@@H:4]([CH:5]([CH3:7])[CH3:6])[C:3]([OH:42])=[O:2])(=[O:10])=[O:11])=[CH:17][CH:16]=4)=[CH:23][CH:22]=3)=[O:26])=[C:31]([CH3:32])[C:30]=2[C:33]=1[O:40][CH3:41])(=[O:39])[CH3:38]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68715677(S)-2-{4'-[(5-acetyl-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

Product 1

HCID 11467313(S)-2-{4'-[(5-acetyl-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acidYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (S)-2-{4′-[(5-acetyl-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester (89 mg) was added 1 mL of THF and 3 mL of LiOH solution (3.6 g LiOH/50 mL MeOH/50 mL H2O). The mixture was stirred at room temperature for 2 days. The solvents were removed under vacuum and the residue was triturated with 4 mL of 2N HCl and filtered. The solid product was dried under vacuum to give 54 mg of (S)-2-{4′-[(5-acetyl-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid was obtained as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (dd, J=12.9, 6.8 Hz, 6 H) 2.0 (m, 1 H) 2.7 (s, 3 H) 2.9 (s, 3 H) 3.6 (dd, J=9.3, 6.1 Hz, 1 H) 4.0 (s, 3 H) 7.0 (d, J=8.8 Hz, 1 H) 7.8 (m, 4 H) 7.9 (m, 4 H) 8.0 (d, J=8.6 Hz, 1 H) 8.1 (d, J=9.3 Hz, 1 H) 10.3 (s, 1 H) 12.6 (s, 1 H).

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was triturated with 4 mL of 2N HCl
  3. filtrationfiltered
  4. customThe solid product was dried under vacuum

Sources & evidence

ORD record
ord-414f172d1b044bad8efab0533d0721bb
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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