Lithium Hydroxide → HCID 11192618, compound

HRID 29377Notes

Reaction equation

HRID 29377 reaction equation
C[O:2][C:3](=[O:43])[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]([N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]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>[CH3:6][CH:5]([CH3:7])[C@H:4]([NH:8][S:9]([C:12]1[CH:13]=[CH:14][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]([N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)[C:30]=4[C:31]=3[CH3:32])=[O:26])=[CH:20][CH:19]=2)=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:3]([OH:43])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68712374(S)-3-methyl-2-{4'-[(3-methyl-4-morpholin-4-yl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid methyl ester

Product 1

HCID 11192618HCID 11192618, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 160 mg of (S)-3-methyl-2-{4′-[(3-methyl-4-morpholin-4-yl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid methyl ester 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 4 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 150 mg of (S)-3-methyl-2-{4′-[(3-methyl-4-morpholin-4-yl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid, obtained as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (dd, J=14.1, 6.8 Hz, 6 H) 2.0 (dd, J=12.1, 6.8 Hz, 1 H) 2.8 (s, 3 H) 3.0 (m, 4 H) 3.5 (m, 1 H) 3.8 (m, 4 H) 7.0 (d, J=7.8 Hz, 1 H) 7.4 (d, J=8.3 Hz, 1 H) 7.4 (m, 1 H) 7.8 (d, J=8.6 Hz, 2 H) 7.8 (m, 4 H) 8.0 (d, J=9.1 Hz, 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-2b601d3f7afb416f91a23b689a6a7e3c
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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