Hydrochloric Acid → HCID 86697388, compound

HRID 237718Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]2[C:31]([CH3:32])=[CH:30][C:29]([OH:33])=[CH:28][C:27]=2[CH3:34])=[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.C([O-])([O-])=O.[Cs+].[Cs+].[O:41]1[C:43]2([CH2:48][CH2:47][S:46][CH2:45][CH2:44]2)[CH2:42]1.Cl>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]2[C:31]([CH3:32])=[CH:30][C:29]([O:33][CH2:42][C:43]3([OH:41])[CH2:48][CH2:47][S:46][CH2:45][CH2:44]3)=[CH:28][C:27]=2[CH3:34])=[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

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-((S)-6-((R)-7-fluoro-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (100 mg) in N,N-dimethylformamide (2 mL) is added Cs2CO3 (106 mg) and 1-oxa-6-thiaspiro[2.5]octane (37 mg). The mixture is stirred for 12 hour at 100° C. The mixture is diluted with water, acidified with 1 M aqueous HCl solution and extracted twice with ethyl acetate. The combined organic phases are washed with water and brine, dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate/methanol 80:20:0→0:80:20) to give the title compound. Yield: 31 mg; LC (method 7): tR=1.16 min; Mass spectrum (ESI+): m/z=579 [M+H]+.

Workup

extractionextracted twice with ethyl acetate
washThe combined organic phases are washed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate/methanol 80:20:0→0:80:20)

Sources & evidence

ORD record: ord-7b845a88ba7247e9a3997e0c1abbad08
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642585B2

Reaction notes

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