Hydrochloric Acid → HCID 86700798, compound

HRID 2406533Notes

Reaction equation

HRID 2406533 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH2:28][C:29]5[CH:34]=[CH:33][C:32]([O:35]C(=O)C)=[CH:31][CH:30]=5)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.C([O-])([O-])=O.[K+].[K+].Cl>CO>[CH3:1][O:2][C:3](=[O:39])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH2:28][C:29]5[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=5)[C:20]([C:24]([F:25])([F:26])[F:27])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86700797HCID 86700797, compound

Product 1

HCID 86700798HCID 86700798, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of {(S)-6-[(R)-4-(4-acetoxy-benzyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (0.19 g), K2CO3 (0.08 g), and methanol (5 ml) is stirred at room temperature for 2 h. The solution is neutralized with 1 N aqueous HCl solution and concentrated. Water is added to the residue, and the resulting mixture is extracted with ethyl acetate. The combined extract is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate) to give the title compound. LC (method 8): tR=1.22 min; Mass spectrum (ESI+): m/z=521 [M+Na]+.

Workup

  1. concentrationconcentrated
  2. additionWater is added to the residue
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. extractionThe combined extract
  5. dry with materialis dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-3af0307998764764999748bf038f8ade
Source dataset
uspto-grants-2014_08
Patent number
US08809376B2

Reaction notes

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