Sodium Hydroxide → 4-[(S)-3-tert-Butoxycarbonylaminopyrrolidin-1-yl]-3-chloro-2-cyclopropylamino-5-fluoro-benzoic acid

HRID 10296Notes

Reaction equation

C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[C:7]([Cl:25])[C:6]=1[NH:26][CH:27]1[CH2:29][CH2:28]1)C.[OH-].[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[C:21]([O:20][C:18]([NH:17][C@H:14]1[CH2:15][CH2:16][N:12]([C:8]2[C:9]([F:11])=[CH:10][C:5]([C:4]([OH:30])=[O:3])=[C:6]([NH:26][CH:27]3[CH2:28][CH2:29]3)[C:7]=2[Cl:25])[CH2:13]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-3-chloro-2-cyclopropylamino-5-fluorobenzoic acid ethyl ester (Example 3c, 2.90 g, 6.56 mmol) in methanol (30 mL) and tetrahydrofuran (30 mL) is added a 1N solution of sodium hydroxide (50 mL). The reaction mixture is stirred at 80° C. for 20 hours, cooled to room temperature, and diluted with ethyl acetate. The organic layer is washed with 1N hydrochloric acid, water, and brine. The organic layer is dried over MgSO4, filtered, and filtrate concentrated to the title compound as a solid (2.74 g). MS CI: m/z 414 (MH+).

Workup

temperaturecooled to room temperature
washThe organic layer is washed with 1N hydrochloric acid, water, and brine
dry with materialThe organic layer is dried over MgSO4
filtrationfiltered
concentrationfiltrate concentrated to the title compound as a solid (2.74 g)

Sources & evidence

ORD record: ord-ad384940417e4d18b0bae0170e802d31
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094780B1

Reaction notes

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