HCID 86697381, compound → HCID 86697380, compound

HRID 237710Notes

Reaction equation

HRID 237710 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH2:34][CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])[C:27]=2[CH3:40])=[C:6]2[C:10]=1[C@H:9]([O:11][C:12]1[CH:25]=[CH:24][C:15]3[C@H:16]([CH2:19][C:20]([O:22]C)=[O:21])[CH2:17][O:18][C:14]=3[CH:13]=1)[CH2:8][CH2:7]2>CO.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH2:34][CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])[C:27]=2[CH3:40])=[C:6]2[C:10]=1[C@H:9]([O:11][C:12]1[CH:25]=[CH:24][C:15]3[C@H:16]([CH2:19][C:20]([OH:22])=[O:21])[CH2:17][O:18][C:14]=3[CH:13]=1)[CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 86697381HCID 86697381, compound2×

Product 1

HCID 86697380HCID 86697380, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 2-((3S)-6-((1R)-7-fluoro-4-(2-methyl-3-(3-(methylsulfonyl)propoxy)phenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (Intermediate 28-32; 64 mg) in methanol (3 mL) and aqueous NaOH (1 M; 0.5 mL) is stirred for 16 hours, concentrated under vacuum, acidified with aqueous HCl (1 M) and extracted with diethyl ether. A precipitate that forms is collected by filtration, washed with some n-hexane, dried and subsequently triturated with a mixture of n-hexane and diethyl ether to give the title compound (30 mg). LC (method 20): tR=6.15 min; Mass spectrum: m/z=555 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with diethyl ether
  3. filtrationA precipitate that forms is collected by filtration
  4. washwashed with some n-hexane
  5. customdried
  6. customsubsequently triturated with a mixture of n-hexane and diethyl ether

Sources & evidence

ORD record
ord-3d2d9d29f689462e850e62900c0f6f71
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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