Water → HCID 59615411, compound

HRID 1425397Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:16][CH2:15][N:14]([C:17]3[S:18][C:19]([C:23]([O:25]CC)=[O:24])=[C:20]([CH3:22])[N:21]=3)[CH2:13]2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+].O>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:16][CH2:15][N:14]([C:17]3[S:18][C:19]([C:23]([OH:25])=[O:24])=[C:20]([CH3:22])[N:21]=3)[CH2:13]2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

Conditions

Temperature: 40 °C

Procedure

Ethyl 2-[(3S)-3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}pyrrolidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (237b) (215 mg, 0.52 mmol) was dissolved in methanol (5 mL). A 2 N aqueous lithium hydroxide solution (2.61 mL, 5.22 mmol) was added, and the mixture was stirred at 40° C. for two hours. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (5 mL) was added to the aqueous layer. The precipitated solid was collected by filtration and washed with water and ethyl acetate to obtain 155 mg of the title compound as a white solid (77%).

Workup

washthe mixture was washed with ethyl acetate
additionA 1 N aqueous hydrochloric acid solution (5 mL) was added to the aqueous layer
filtrationThe precipitated solid was collected by filtration
washwashed with water and ethyl acetate

Sources & evidence

ORD record: ord-4aa41d87aba6442093ab63901058d248
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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