Water → HCID 68292560, compound

HRID 2276927Notes

Reaction equation

HRID 2276927 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C@@H:24]4[O:29][C:28]5[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=5[O:26][CH2:25]4)=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[OH:35][Li].O.[O:38]1[CH2:43]COCC1.O>C(O)(=O)C>[O:29]1[C:28]2[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=2[O:26][CH2:25][C@@H:24]1[C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:14]2[CH2:13][CH2:12][N:11]([CH2:10][C:7]3[CH:8]=[C:9]([CH:4]=[CH:5][CH:6]=3)[C:43]([OH:38])=[O:35])[CH2:16][CH2:15]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 68292076HCID 68292076, compound

Product 1

HCID 68292560HCID 68292560, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-{4-[(S)-4-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-piperazin-1-ylmethyl}-benzoic acid methyl ester (48 mg, 0.11 mmol), LiOH.H2O (15 mg, 0.37 mmol), dioxane (5 mL), and water (0.5 mL) is stirred at room temperature for 16 h. The reaction mixture is neutralized with acetic acid and concentrated. The residue is triturated with water to give the title compound (LCMS method 4: ES+ m/z 445.2 [M+H]+, Rt=1.31 min).

Workup

  1. concentrationconcentrated
  2. customThe residue is triturated with water

Sources & evidence

ORD record
ord-a6179a10fdb34dfab60fb2777b708dd0
Source dataset
uspto-grants-2015_09
Patent number
US09133146B2

Reaction notes

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