Sodium Bicarbonate → HCID 59331315, compound

HRID 1882021Notes

Reaction equation

HRID 1882021 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[C:14](=O)[CH:15]([CH2:21][C:22](=O)[C:23]3[S:24][CH:25]=[CH:26][N:27]=3)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:41].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14]3[NH:41][C:22]([C:23]4[S:24][CH:25]=[CH:26][N:27]=4)=[CH:21][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 59331605HCID 59331605, compound

Product 1

HCID 59331315HCID 59331315, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 4-[4-(cyclopropylsulfonyl)phenyl]-3-oxo-2-[2-oxo-2-(1,3-thiazol-2-yl)ethyl]-5-(tetrahydro-2H-pyran-4-yl)pentanoate (0.190 g) in acetic acid (5 mL) was added ammonium acetate (0.411 g) at room temperature, and the mixture was stirred at 100° C. for 15 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30, volume ratio) to give the title compound (0.126 g, yield 68%) as a colorless amorphous solid. MS: 515 (MH+). melting point 178-179° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30, volume ratio)

Sources & evidence

ORD record
ord-1a070e97b98f47e49ede4262b42270e8
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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