Hydrochloric Acid → HCID 25117747, compound

HRID 1664696Notes

Reaction equation

HRID 1664696 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[S:11][CH:12]=[C:13]([C@H:15]3[CH2:20][CH2:19][CH2:18][CH2:17][N:16]3[C:21](=[O:30])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:14]=2)[CH:5]=1.[OH-].[K+].Cl>CO.O>[O:23]([CH2:22][C:21]([N:16]1[CH2:17][CH2:18][CH2:19][CH2:20][C@@H:15]1[C:13]1[N:14]=[C:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:31])=[O:2])[S:11][CH:12]=1)=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 25122351HCID 25122351, compound

Product 1

HCID 25117747HCID 25117747, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-{4-[(R)-1-(2-phenoxy-acetyl)-piperidin-2-yl]-thiazol-2-yl}-benzoic acid methyl ester (0.030 g, 0.069 mmol) (prepared as illustrated in example 24) in methanol (0.5 mL) was treated with 1N KOH (0.14 mL, 0.14 mmol). The mixture was stirred at room temperature for 16 h, then diluted with water (0.5 mL) and acidified to pH 1 with HCl 0.5N. A white solid precipitated, which was filtered to yield 3-{4-[(R)-1-(2-phenoxy-acetyl)-piperidin-2-yl]-thiazol-2-yl}-benzoic acid (0.022 g, 76%), MS (ISP): 421.3 (M−H). 1H-NMR (CDCl3, 300 MHz): 13.33 (1H, bs), 8.44 (1H, s), 8.15 (1H, d), 8.04 (1H, d), 7.65 (1H, m), 7.23 (2H, m), 6.92 (3H, m), 5.76+5.33 (1H, bs), 4.94 (2H, m), 4.34+3.80 (1H, bd), 3.32 (3H, m), 1.64 (4H, m).

Workup

  1. customA white solid precipitated
  2. filtrationwhich was filtered

Sources & evidence

ORD record
ord-9c55c1ed57a245d0bf4d6a84a78bd963
Source dataset
uspto-grants-2011_10
Patent number
US08039487B2

Reaction notes

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