Sodium Hydroxide → HCID 57507813, compound

HRID 2074277Notes

Reaction equation

[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:37]=[CH:38][CH:39]=1)[CH2:7][O:8][C:9]1[CH:36]=[CH:35][C:12]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]3[CH:24]=[N:25][CH:26]=[C:27](/[CH:29]=[CH:30]/[C:31]([O:33]C)=[O:32])[CH:28]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([CH:37]=[CH:38][CH:39]=1)[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]3[CH:28]=[C:27](/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32])[CH:26]=[N:25][CH:24]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 60 °C

Procedure

An aqueous 1 M sodium hydroxide solution (1.11 ml) was added to a THF (5 ml) solution containing 5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridin-3-yl 4-{4-[(3-fluorobenzyl)oxy]phenoxy}piperidine-1-carboxylate (158 mg), followed by stirring at 60° C. for 3 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 (v/v)) to obtain (2E)-3-(5-{[(4-{4-[(3-fluorobenzyl)oxy]phenoxy}piperidin-1-yl)carbonyl]oxy}pyridin-3-yl)acrylic acid (88 mg).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 (v/v))

Sources & evidence

ORD record: ord-9c6aae5c2efa4a34a8b3c36b5dce2fe3
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919494B2

Reaction notes

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