Sodium Hydroxide → {(S)-6-[(R)-7-Fluoro-4-phenoxy-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid

HRID 2408577Notes

Reaction equation

HRID 2408577 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:34])[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]([O:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:22]=[CH:23][C:24]=4[F:26])[CH2:19][CH2:18]3)=[CH:15][C:10]=2[O:9][CH2:8]1>CO.O1CCCC1>[F:26][C:24]1[CH:23]=[CH:22][C:21]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:20]2[C:25]=1[C@H:17]([O:16][C:14]1[CH:13]=[CH:12][C:11]3[C@H:7]([CH2:6][C:5]([OH:34])=[O:4])[CH2:8][O:9][C:10]=3[CH:15]=1)[CH2:18][CH2:19]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86720105{(S)-6-[(R)-7-Fluoro-4-phenoxy-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 85468847{(S)-6-[(R)-7-Fluoro-4-phenoxy-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 M aqueous NaOH solution (3.0 mL) is added to a solution of {(S)-6-[(R)-7-fluoro-4-phenoxy-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (0.18 g) in methanol (6 mL) and tetrahydrofuran (6 mL) at room temperature. The mixture is stirred at room temperature for 4 h. The organic solvent is evaporated, water (2 mL) is added, and the resulting solution is neutralized with 1 M aqueous HCl solution (3 mL). The solution is stirred at room temperature for 1 h. The precipitate is separated by filtration, washed with water and dried to give the title compound (if the compound does not precipitate, the solution is concentrated and the residue is purified by HPLC on reversed phase using acetonitrile, water and ammonia as eluent). LC (method 3): tR=1.14 min; Mass spectrum (ESI−): m/z=419 [M−H]−.

Workup

  1. customThe organic solvent is evaporated
  2. additionwater (2 mL) is added
  3. stirringThe solution is stirred at room temperature for 1 h
  4. customThe precipitate is separated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-abc1f91a3efa4cf4b7925465d5efbb28
Source dataset
uspto-grants-2014_08
Patent number
US08815864B2

Reaction notes

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