Hydrochloric Acid → HCID 59331293, compound

HRID 1882060Notes

Reaction equation

HRID 1882060 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27][C:28]([CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[CH:29][N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[OH-].[Na+].Cl.[Cl-].[Ca+2].[Cl-]>O.CO.O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27][C:28]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:29][N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 5284359Calcium ChlorideHCID 59331231HCID 59331231, compound

Product 1

HCID 59331293HCID 59331293, compoundYield 77.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]propanoate (0.46 g), 1M aqueous sodium hydroxide solution (1.7 mL), methanol (3 mL) and tetrahydrofuran (6 mL) was stirred at room temperature overnight. To the reaction mixture was added 1M hydrochloric acid (1.7 mL), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a yellow amorphous solid. To a mixture of the obtained amorphous solid, 1M aqueous sodium hydroxide solution (1.0 mL), methanol (1 mL) and water (10 mL) was added a solution of calcium chloride (94 mg) in water (2 ml). The precipitated solid was collected by filtration, washed with water, and dried to give the title compound (0.34 g) as yellow crystals. melting point>194° C. (decomposition). MS: 515 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a yellow amorphous solid
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d2ef7274a8e9470ebc44ae6959ac3dc8
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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