Sodium Hydroxide → (2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)acrylic acid

HRID 2376003Notes

Reaction equation

[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([N:8]2[CH2:12][CH2:11][CH:10]([NH:13][C:14]3[S:15][CH:16]=[C:17](/[CH:19]=[CH:20]/[C:21]([O:23]CC)=[O:22])[N:18]=3)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:12][CH2:11][CH:10]([NH:13][C:14]3[S:15][CH:16]=[C:17](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])[N:18]=3)[CH2:9]2)=[O:7])=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The mixture of ethyl (2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)acrylate (0.9 g) and 1N-NaOH (4.4 mL) in MeOH (14 mL) was stirred at 50° C. for 3 hours and the mixture was evaporated in vacuo. To the residue was added a solution of AcOEt, THF and water, and the mixture was adjusted to pH 4 with 1N-HCl. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give (2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)acrylic acid (0.64 g).

Workup

customthe mixture was evaporated in vacuo
additionTo the residue was added a solution of AcOEt, THF and water
washThe separated organic layer was washed with water
dry with materialdried over magnesium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-ab8a8fbebfe447638f9031bb496976c7
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465731B2

Reaction notes

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