Hydrochloric Acid → HCID 11698688, compound

HRID 2356818Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([NH:27][C@H:28]([C:32]([O:34]C)=[O:33])[CH:29]([CH3:31])[CH3:30])=[O:26])=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.CO.[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([NH:27][C@H:28]([C:32]([OH:34])=[O:33])[CH:29]([CH3:31])[CH3:30])=[O:26])=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl N-({3′-fluoro-4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]biphenyl-4-yl}carbonyl)-L-valinate (84.2 mg, 0.17 mmol) was suspended in THF (2.5 mL), MeOH (2.5 mL) and water (1 mL), and LiOH (40.7 mg, 1.70 mmol) was added. The reaction mixture was heated at 50° C. for 2 h. Upon cooling to rt, the reaction mixture was brought to pH 3 with 1N HCl and was extracted with EtOAc (3×25 mL). The combined organic phases were washed with water (2×50 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. This yielded 72.3 mg (88%) of the title compound as a white solid. LC/MS m/z 482.3 (MH+), retention time 3.46 min. 1H NMR (400 MHz, DMSO-d6) δ 0.99 (dd, 6H), 2.19-2.24 (m, 1H), 4.30 (dd, H), 7.18 (t, 1H), 7.60-7.84 (m, 6H), 7.88 (d, 2H), 8.42 (d, 1H), 8.66 (t, 1H), 10.42 (s, 1H).

Workup

temperatureUpon cooling to rt
extractionwas extracted with EtOAc (3×25 mL)
washThe combined organic phases were washed with water (2×50 mL) and brine (50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-25a1c7a1f9694c71b12f24f99f47ed40
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759376B2

Reaction notes

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