Hydrochloric Acid → HCID 59331425, compound

HRID 1881971Notes

Reaction equation

HRID 1881971 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:36]3[NH:40][C:39]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=4)=[CH:38][CH:37]=3)[CH2:14][C@H:15]3[CH2:35][CH2:34][C:17]4(O[C@H](C5C=CC=CC=5)[C@@H](C5C=CC=CC=5)[O:18]4)[CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.Cl>O1CCCC1.C(OCC)(=O)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:36]3[NH:40][C:39]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=4)=[CH:38][CH:37]=3)[CH2:14][C@H:15]3[CH2:35][CH2:34][C:17](=[O:18])[CH2:16]3)=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59331377HCID 59331377, compound

Product 1

HCID 59331425HCID 59331425, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]ethyl}-1H-pyrrol-2-yl)pyridine (70 mg) in tetrahydrofuran (3 mL) was added 1M hydrochloric acid (3 mL), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (45 mg, yield 94%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 435 (MH+).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-60294b26ab044ec69927364ab6f6e769
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…