Sodium Hydroxide → {(S)-6-[(R)-4-Morpholin-4-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid

HRID 1422637Notes

Reaction equation

HRID 1422637 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:37])[CH2:6][C@H:7]1[C:11]2[CH:12]=[CH:13][C:14]([O:16][C@H:17]3[C:25]4[C:20](=[C:21]([CH2:30][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)[C:22]([C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)=[CH:15][C:10]=2[O:9][CH2:8]1>CO.O1CCCC1>[N:31]1([CH2:30][C:21]2[C:22]([C:26]([F:27])([F:29])[F:28])=[CH:23][CH:24]=[C:25]3[C:20]=2[CH2:19][CH2:18][C@H:17]3[O:16][C:14]2[CH:13]=[CH:12][C:11]3[C@H:7]([CH2:6][C:5]([OH:37])=[O:4])[CH2:8][O:9][C:10]=3[CH:15]=2)[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 90313207{(S)-6-[(R)-4-Morpholin-4-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydrobenzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 90314216{(S)-6-[(R)-4-Morpholin-4-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4 M aqueous NaOH solution (0.20 mL) is added to a solution of {(S)-6-[(R)-4-morpholin-4-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (91 mg) in methanol (1 mL) and tetrahydrofuran (1 mL) at room temperature. The mixture is stirred at room temperature for 3 h. The organic solvent is evaporated, water is added to the residue, and the resulting solution is neutralized with 1 M aqueous HCl solution. The solution is stirred at room temperature for 1 h. The precipitate formed is separated by filtration, washed with water, and dried to give the title compound (if the title compound does not precipitate, the solution is concentrated, and the residue is purified by HPLC on reversed phase using acetonitrile and water as eluent). LC (method 1): tR=0.94 min; Mass spectrum (ESI+): m/z=478 [M+H]+.

Workup

  1. customThe organic solvent is evaporated
  2. additionwater is added to the residue
  3. stirringThe solution is stirred at room temperature for 1 h
  4. customThe precipitate formed
  5. customis separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-f1416e290447450fa3d812666efd6f03
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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