Hydrochloric Acid → HCID 59570996, compound

HRID 2192955Notes

Reaction equation

HRID 2192955 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:17]([NH:19][C:20]3[CH:25]=[N:24][C:23]([CH:26]4[CH2:30][O:29]C(C)(C)[O:27]4)=[CH:22][N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.Cl>C1COCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:17]([NH:19][C:20]3[CH:25]=[N:24][C:23]([CH:26]([OH:27])[CH2:30][OH:29])=[CH:22][N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:14][CH2:15]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59570912HCID 59570912, compound

Product 1

HCID 59570996HCID 59570996, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-N-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyrazin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide (150 mg) in THF (10 mL) was added 1 M hydrochloric acid at room temperature, followed by stirring at room temperature for 3 hours. After extraction with ethyl acetate, the organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-N-[5-(1,2-dihydroxyethyl)pyrazin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide (133 mg) as a white amorphous substance.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washthe organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-20d6e24224ff40f18d718237ba5b7110
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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