Lithium hydroxide, monohydrate → HCID 22057727, compound

HRID 1828698Notes

Reaction equation

HRID 1828698 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][S:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:20]([C:30]([F:33])([F:32])[F:31])[CH:19]=3)=[CH:12][CH:11]=2)[CH2:6]1)=[O:4].O[Li].O>CO.O>[F:32][C:30]([F:31])([F:33])[C:20]1[CH:19]=[C:18]([S:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([CH2:9][N:7]3[CH2:8][CH:5]([C:3]([OH:4])=[O:2])[CH2:6]3)=[CH:11][CH:12]=2)[CH:23]=[CH:22][C:21]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69135040HCID 69135040, compound

Product 1

HCID 22057727HCID 22057727, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-[4-(2-trifluoromethyl-biphenyl-4-ylsulfanylmethyl)-benzyl]-azetidine-3-carboxylic acid methyl ester (129 mg, 0.2736 mmol, 1 eq.) in a mixture of MeOH (5 mL) and H2O (0.5 mL) is added LiOH—H2O (23 mg, 0.5472 mmol, 2 eq.). The mixture is stirred at room temperature for 3 h. After concentration, the crude product is purified by preparative RP LC-MS to give 1-[4-(2-Trifluoromethyl-biphenyl-4-ylsulfanylmethyl)-benzyl]-azetidine-3-carboxylic acid: 1H NMR (CD3OD, 400 MHz) δ7.61 (s, 1H), 7.60 (d, 1H), 7.56 (d, 2H), 7.46–7.39 (m, 6H), 7.29 (d, 2H), 4.42 (s, 2H), 4.35 (s, 2H), 4.31 (d, 4H), 3.73–3.61 (m, 1H); MS (ES+): (458.1, M+1)+.

Workup

  1. concentrationAfter concentration
  2. customthe crude product is purified by preparative RP LC-MS

Sources & evidence

ORD record
ord-63d1b4239cb9446e882d532060e12120
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Reaction notes

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