Hydrochloric Acid → (3R)-3-{2-[3-chloro-4-(methylsulfonyl)phenyl]-2-(5-(pyrazin-2-yl)-1H-pyrrol-2-yl)ethyl}cyclopentanone

HRID 1882083Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([C:35]2[NH:39][C:38]([C:40]3[CH:45]=[N:44][CH:43]=[CH:42][N:41]=3)=[CH:37][CH:36]=2)[CH2:13][C@H:14]2[CH2:34][CH2:33][C:16]3(O[C@H](C4C=CC=CC=4)[C@@H](C4C=CC=CC=4)[O:17]3)[CH2:15]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].Cl.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([C:35]2[NH:39][C:38]([C:40]3[CH:45]=[N:44][CH:43]=[CH:42][N:41]=3)=[CH:37][CH:36]=2)[CH2:13][C@H:14]2[CH2:34][CH2:33][C:16](=[O:17])[CH2:15]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-(5-{1-[3-chloro-4-(methylsulfonyl)phenyl]-2-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]ethyl}-1H-pyrrol-2-yl)pyrazine (94.3 mg) in tetrahydrofuran (1 mL) was added 1M hydrochloric acid (1 mL), and the mixture was stirred at 50° C. for 24 hr. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (44.7 mg, yield 68%) was obtained as a white amorphous solid from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio). MS: 444 (MH+).

Workup

temperatureAfter cooling to room temperature
washwashed with water
dry with materialThe ethyl acetate layer was dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-c60a61ea01f64841959142a8402d5784
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318746B2

Reaction notes

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