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

HRID 2091363
Notes
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Reaction equation

HRID 2091363 reaction equation
[CH:1]1([CH:7]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([NH:36][CH2:37][CH2:38][C:39]([O:41]CC)=[O:40])=[O:35])=[CH:30][CH:29]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([F:26])[CH:21]=4)=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([CH:7]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([NH:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[O:35])=[CH:30][CH:29]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([F:26])[CH:21]=4)=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66777071Ethyl 3-[({4-[(cyclohexyl{5-[(2-fluoropyridin-4-yl)methoxy]-3-methyl-1-benzofuran-2-yl}methyl)amino]phenyl}carbonyl)amino]propanoate2×

Product 1

HCID 667779653-[({4-[(Cyclohexyl{5-[(2-fluoropyridin-4-yl)methoxy]-3-methyl-1-benzofuran-2-yl}methyl)amino]phenyl}carbonyl)amino]propanoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

Ethyl 3-[({4-[(cyclohexyl{5-[(2-fluoropyridin-4-yl)methoxy]-3-methyl-1-benzofuran-2-yl}methyl)amino]phenyl}carbonyl)amino]propanoate (0.24 g) synthesized in the above-mentioned (2) 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 (0.17 g, 75%) 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-6291dab07c474374a91b1482c222f861
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08436043B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes