Methanol → (S)-2-(2-(2-(3-(1H-tetrazol-5-yl)phenyl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol

HRID 510312Notes

Reaction equation

C([O:7][CH2:8][C@H:9]([C:15]1[C:40]([CH3:41])=[CH:39][C:18]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]5[NH:38][N:37]=[N:36][N:35]=5)[CH:29]=4)[CH:23]=3)[S:21][C:17]=2[C:16]=1[C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=O)C(C)(C)C.CO.[OH-].[Na+]>C1COCC1>[NH:38]1[C:34]([C:30]2[CH:29]=[C:28]([C:24]3[CH:23]=[C:22]([C:20]4[S:21][C:17]5[C:16]([C:42]6[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=6)=[C:15]([C@H:9]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:8][OH:7])[C:40]([CH3:41])=[CH:39][C:18]=5[N:19]=4)[CH:27]=[CH:26][N:25]=3)[CH:33]=[CH:32][CH:31]=2)=[N:35][N:36]=[N:37]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of crude (S)-2-(2-(2-(3-(1H-tetrazol-5-yl)phenyl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate from the previous reaction (assume 0.027 mmol) in THF (0.4 mL) and methanol (0.4 mL) was added NaOH (0.4 mL of a 2N solution). The reaction mixture was heated at 40° C. for 2 h, cooled, quenched with NH4Cl (sat. aq.), and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated to give the crude product which was used without further purification. LCMS-ESI+: calc'd for C32H30ClN6O2S: 597.2 (M+H+); Found: 597.0 (M+H+).

Workup

temperaturecooled
customquenched with NH4Cl (sat. aq.)
extractionextracted with ethyl acetate
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-73d91409e20a4e45a44fe6ae0b44b0c2
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096586B2

Reaction notes

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