Sodium Hydroxide → HCID 66777933, compound

HRID 2091415Notes

Reaction equation

[CH3:1][N:2]([C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH:19]([C:23]2[O:24][C:25]3[CH:32]=[CH:31][C:30]([O:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][N:35]=4)=[CH:29][C:26]=3[C:27]=2[CH3:28])[CH:20]([CH3:22])[CH3:21])=[CH:14][CH:13]=1)=[O:11])[CH2:3][CH2:4][C:5]([O:7]CC)=[O:6].[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]([C:10]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][CH:19]([C:23]2[O:24][C:25]3[CH:32]=[CH:31][C:30]([O:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][N:35]=4)=[CH:29][C:26]=3[C:27]=2[CH3:28])[CH:20]([CH3:22])[CH3:21])=[CH:16][CH:17]=1)=[O:11])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 3-{methyl[(4-{[2-methyl-1-(3-methyl-5-{[5-(trifluoromethyl)pyridin-2-yl]oxy}-1-benzofuran-2-yl)propyl]amino}phenyl)carbonyl]amino}propanoate (425 mg) synthesized in Example A205 was dissolved in tetrahydrofuran (4.0 mL), 1N aqueous sodium hydroxide solution (1.4 mL) was added to the solution, and the mixture was stirred at 50° C. for 1.5 hr. The solvent was evaporated under reduced pressure, water (4 mL) was added to the residue, and the mixture was neutralized with 1N hydrochloric acid (1.4 mL) under ice-cooling and stirred for 20 min. The resulting precipitate was collected by filtration, and dried to give the title compound (378 mg, 94%) as a colorless amorphous form.

Workup

customThe solvent was evaporated under reduced pressure, water (4 mL)
additionwas added to the residue
temperaturecooling
stirringstirred for 20 min
filtrationThe resulting precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-6e60bc6edb644765a59805a059f796fd
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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