Water → HCID 178461179, compound

HRID 2103725Notes

Reaction equation

HRID 2103725 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

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 178497325HCID 178497325, compound

Product 1

HCID 178461179HCID 178461179, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customSolvent and excess of water were removed
  2. additionHCl (2N) was added
  3. customExcess of water was removed
  4. customThe solid was triturated with CH2Cl2/MeOH
  5. filtrationfiltrated
  6. customThe solvents of the filtrate were removed under vacuum
  7. additionThe residue was treated with CH2Cl2
  8. filtrationfiltrated again
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-11cac81a62884741b1704dd1ab2a15d7
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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