Water → HCID 24993409, compound

HRID 423580Notes

Reaction equation

HRID 423580 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[OH:30]OS([O-])=O.[K+].[OH2:36]>CC(C)=O>[CH3:1][S:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)(=[O:30])=[O:36]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 66672986HCID 66672986, compound

Product 1

HCID 24993409HCID 24993409, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The title compound (26 mg, 78%) was prepared as a white solid from 1-methylethyl 4-{[(6-{4-[(methylthio)methyl]phenyl}-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (31 mg, 0.07 mmol) and Oxone® (0.19 g, 0.3 mmol) in acetone (4 mL) and water (1.5 mL) in a manner similar to Example 81, Step 4. The crude product was triturated with hot hexane containing 1% of MeOH to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.37 (d, 1H, J=2.7 Hz), 7.97 (d, 2H, J=8.1 Hz), 7.67 (d, 1H, J=8.8 Hz), 7.49 (d, 2H, J=8.3 Hz), 7.30-7.20 (m, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.29 (s, 2H), 4.22 (bs, 2H), 3.90 (d, 2H, J=6.3 Hz), 2.85-2.70 (m, 5H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (ESI), m/z 447 (M+H).

Workup

  1. customThe crude product was triturated with hot hexane containing 1% of MeOH

Sources & evidence

ORD record
ord-1df73204e193477bb7cca69dcc27a75a
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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