Sodium Hydroxide → 3-{[(4-{[{5-[(6-Chloropyridin-3-yl)methoxy]-3-methyl-1-benzofuran-2-yl}(cyclohexyl)methyl]amino}phenyl)carbonyl]amino}propanoic acid

HRID 2091366Notes

Reaction equation

HRID 2091366 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])=[O:33])=[CH:28][CH:27]=4)[CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[C:15]([CH3:42])[C:14]=3[CH:43]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]([NH:25][C:26]4[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[CH:30][CH:31]=4)[CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[C:15]([CH3:42])[C:14]=3[CH:43]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86662754Ethyl 3-{[(4-{[{5-[(6-chloropyridin-3-yl)methoxy]-3-methyl-1-benzofuran-2-yl}(cyclohexyl)methyl]amino}phenyl)carbonyl]amino}propanoate2×

Product 1

HCID 866627553-{[(4-{[{5-[(6-Chloropyridin-3-yl)methoxy]-3-methyl-1-benzofuran-2-yl}(cyclohexyl)methyl]amino}phenyl)carbonyl]amino}propanoic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-{[(4-{[{5-[(6-chloropyridin-3-yl)methoxy]-3-methyl-1-benzofuran-2-yl}(cyclohexyl)methyl]amino}phenyl)carbonyl]amino}propanoate (0.31 g) synthesized in the above-mentioned (1) was dissolved in ethanol (3 mL), 1N aqueous sodium hydroxide solution (1.0 mL) was added to the solution at room temperature, and the mixture was stirred at room temperature for 0.5 hr. Ethanol was evaporated under reduced pressure, and 1N hydrochloric acid (1.0 mL) was added to the residue. The precipitate was washed with water to give the title object compound (0.22 g, 74%) as a colorless solid.

Workup

  1. customEthanol was evaporated under reduced pressure, and 1N hydrochloric acid (1.0 mL)
  2. additionwas added to the residue
  3. washThe precipitate was washed with water

Sources & evidence

ORD record
ord-61bbbbbec16f4adca77526971359044c
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…