Sodium Hydroxide → HCID 72203367, compound

HRID 2406550Notes

Reaction equation

HRID 2406550 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:35])[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]([CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:22]([C:26]#[N:27])=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)=[CH:15][C:10]=2[O:9][CH2:8]1>CO.O.Cl>[CH2:28]([C:21]1[C:22]([C:26]#[N:27])=[CH:23][CH:24]=[C:25]2[C:20]=1[CH2:19][CH2:18][C@H:17]2[O:16][C:14]1[CH:13]=[CH:12][C:11]2[C@H:7]([CH2:6][C:5]([OH:35])=[O:4])[CH2:8][O:9][C:10]=2[CH:15]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86700815HCID 86700815, compound

Product 1

HCID 72203367HCID 72203367, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

1 M aqueous NaOH solution (0.60 mL) is added to a solution of {(S)-6-[(R)-4-benzyl-5-cyano-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (0.10 g) in methanol (3 mL) at room temperature. The mixture is stirred at 40° C. for 1 h. The mixture is diluted with water and neutralized with 1 M aqueous HCl solution. The resulting mixture is extracted with ethyl acetate, and the combined extract is washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100) to give the title compound. In case the product is insufficiently pure after this procedure the product is submitted to HPLC on reversed phase (MeCN/water). LC (method 4): tR=1.14 min; Mass spectrum (ESI+): m/z=424 [M+H]+.

Workup

  1. extractionThe resulting mixture is extracted with ethyl acetate
  2. extractionthe combined extract
  3. washis washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent is evaporated
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100)

Sources & evidence

ORD record
ord-0cec5d1ef81047b680c3913c936da9b9
Source dataset
uspto-grants-2014_08
Patent number
US08809376B2

Reaction notes

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