Lithium Hydroxide → HCID 11421763, compound

HRID 29373Notes

Reaction equation

HRID 29373 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][CH:34]=[C:33]([C:37]5[CH:41]=[CH:40][O:39][CH:38]=5)[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>[O:39]1[CH:40]=[CH:41][C:37]([C:33]2[C:30]3[C:31]([CH3:32])=[C:27]([C:25]([NH:24][C:21]4[CH:22]=[CH:23][C:18]([C:15]5[CH:16]=[CH:17][C:12]([S:9]([NH:8][C@@H:4]([CH:5]([CH3:6])[CH3:7])[C:3]([OH:42])=[O:2])(=[O:10])=[O:11])=[CH:13][CH:14]=5)=[CH:19][CH:20]=4)=[O:26])[O:28][C:29]=3[CH:36]=[CH:35][CH:34]=2)=[CH:38]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68712301(S)-2-{4'-[(4-furan-3-yl-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

Product 1

HCID 11421763HCID 11421763, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 240 mg of (S)-2-{4′-[(4-furan-3-yl-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester was added 2 mL of THF and 4 mL of LiOH solution (3.6 g LiOH/50 mL MeOH/50 mL H2O). The mixture was stirred at room temperature for 4 days. The solvents were removed under vacuum and the residue was dissolved in 5 mL of water. The solution was acidified to pH2 and the resulting suspension was filtered. The solid product was dried under vacuum to give 171 mg of (S)-2-{4′-[(4-furan-3-yl-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid was obtained as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (dd, J=13.1, 6.8 Hz, 6 H) 2.4 (s, 3 H) 3.5 (m, 1 H) 6.8 (dd, J=1.9, 0.9 Hz, 1 H) 7.2 (dd, J=7.3, 1.0 Hz, 1 H) 7.5 (dd, J=7.6 Hz, 1 H) 7.7 (dd, J=8.5, 0.9 Hz, 1 H) 7.8 (d, J=8.8 Hz, 2 H) 7.8 (m, 4 H) 7.9 (m, 2 H) 7.9 (dd, J=1.5, 0.8 Hz, 1 H) 8.0 (m, 3 H) 10.6 (s, 1 H) 12.6 (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-e659e822825e4eb5b8e0b8a13cd4ca78
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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