Ammonia → HCID 10365007, compound

HRID 854801Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:12]([C:22](=[O:30])[NH:23][C:24]2[CH:29]=[N:28][CH:27]=[CH:26][N:25]=2)[CH2:13][CH:14]2[CH2:18][CH2:17][CH:16]([O:19]C=O)[CH2:15]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].N>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:13][CH:14]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]2)[C:22]([NH:23][C:24]2[CH:29]=[N:28][CH:27]=[CH:26][N:25]=2)=[O:30])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of formic acid 3-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-2-(pyrazin-2-ylcarbamoyl)-ethyl]-cyclopentyl ester (375 mg, 0.83 mmol) in methanol (50 mL) at 0° C. was bubbled ammonia gas for 15 min. The resulting reaction solution was stirred at 0° C. for 15 min. The solvent was removed in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 1-5% methanol/methylene chloride) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-hydroxy-cyclopentyl)-N-pyrazin-2-yl-propionamide (260 mg, 62.5%) as an off-white solid.

Workup

customThe resulting reaction solution
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-7c45be1b547a47e0850d8526b3eb05d9
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259166B2

Reaction notes

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