Methanol → HCID 11562292, compound

HRID 2356835Notes

Reaction equation

[F:1][C:2]1[CH:39]=[CH:38][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([NH:24][C@H:25]([C:29]([O:31]CCCC)=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:23])=[C:18]([O:36][CH3:37])[CH:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.CO.O.[Li+].[OH-]>C1COCC1>[F:1][C:2]1[CH:39]=[CH:38][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([NH:24][C@H:25]([C:29]([OH:31])=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:23])=[C:18]([O:36][CH3:37])[CH:17]=4)=[CH:14][CH:15]=3)[S:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Butyl N-({4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methoxybiphenyl-4-yl}carbonyl)-L-valinate (0.02 g, 0.03 mmol) was suspended in THF (1 mL), MeOH (1 mL) and water (0.5 mL), and then LiOH (0.01 g, 0.35 mmol) was added. The reaction mixture was heated at 50° C. for 3 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure and acidified with 2N HCl. The resulting solid was collected by filtration and purified by HPLC (15-80% CH3CN in H2O/0.1% TFA gradient), yielding 19 mg (91%) of the title compound. LC/MS m/z 494.1 (MH+), retention time 3.47 min. 1H NMR (400 MHz, CD3OD) δ 1.06 (d, 6H), 2.32-2.39 (m, 1H), 4.10 (s, 3H), 4.60 (d, 1H), 7.05 (t, 1H), 7.35-7.58 (m, 4H), 7.60 (d, 2H), 7.80 (d, 2H), 8.05 (d, 1H).

Workup

temperatureUpon cooling to rt
concentrationthe reaction mixture was concentrated under reduced pressure
filtrationThe resulting solid was collected by filtration
custompurified by HPLC (15-80% CH3CN in H2O/0.1% TFA gradient)

Sources & evidence

ORD record: ord-6bcd032b722741b1ad93e5d77bde6715
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759376B2

Reaction notes

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