Water → HCID 178461179, compound

HRID 2047571Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C@H:8]1[CH2:11][C@H:10]([C:12]2[S:13][C:14]3[CH:20]=[C:19]([C:21]([O:23]C)=[O:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH2:9]1.O.C[O-].[Na+]>CO>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C@H:8]1[CH2:9][C@H:10]([C:12]2[S:13][C:14]3[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH2:11]1

Participants

Conditions

Temperature: 23 °C

Procedure

Methyl 2-{trans-3-[(S)-2-methylpiperidin-1-yl]cyclobutyl}-1,3-benzothiazole-6-carboxylate (Example 143A, 2.0 g, 5.8 mmol) was dissolved in methanol (600 mL), followed by H2O (300 mg, 16.7 mmol) and sodium methoxide (1.4 g, 26 mmol) at 23° C. The reaction mixture was then allowed to stir at 23° C. for 1 day. Solvent and excess of water were removed. HCl (2N) was added to make the mixture slightly acidic (pH ˜5-6). Excess of water was removed. The solid was triturated with CH2Cl2/MeOH, and filtrated. The solvents of the filtrate were removed under vacuum. The residue was treated with CH2Cl2 and filtrated again. Removal of the solvent gave the desired product as an off-white solid (2.13 g, 100%). 1H NMR (300 MHz, CD3OD): δ=8.54 ppm (d, J=1.3 Hz, 1H), 8.11 (dd, J=8.9, 1.3 Hz, 1H), 7.91 (d, J=8.9 Hz, 1H), 4.00 (m, 1H), 3.80 (m, 1H), 2.70-3.10 (m, 7H), 2.00 (m, 2H), 1.80 (m, 2H), 1.65 (m, 2H), 1.41 (d, J=6.8 Hz, 3H). MS (ESI, M+H+): 331.0.

Workup

customSolvent and excess of water were removed
additionHCl (2N) was added
customExcess of water was removed
customThe solid was triturated with CH2Cl2/MeOH
filtrationfiltrated
customThe solvents of the filtrate were removed under vacuum
additionThe residue was treated with CH2Cl2
filtrationfiltrated again
customRemoval of the solvent

Sources & evidence

ORD record: ord-60a75522868d4c9d97eff6597ae768c6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592467B2

Reaction notes

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