Methanol → HCID 57860103, compound

HRID 1947164Notes

Reaction equation

HRID 1947164 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[S:25][C:24]3[CH:23]=[C:22]([CH2:26][CH3:27])[N:21]([CH2:28][C:29](=[O:36])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:20](=[O:37])[C:19]=3[C:18]=2[O:38][CH2:39][CH3:40])=[O:16])[CH2:10][CH2:9]1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO.O>C1COCC1>[CH2:39]([O:38][C:18]1[C:19]2[C:20](=[O:37])[N:21]([CH2:28][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:22]([CH2:26][CH3:27])=[CH:23][C:24]=2[S:25][C:17]=1[C:15]([NH:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH2:9][CH2:10]1)=[O:16])[CH3:40]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 66891023HCID 66891023, compound

Product 1

HCID 57860103HCID 57860103, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of 2-[4-({[3-ethoxy-6-ethyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]pyridin-2-yl]carbonyl}amino)piperidin-1-yl]-2-oxoethyl acetate (90 mg, 0.18 mmol) and potassium carbonate (39 mg, 0.28 mmol) in THF (8 mL)-methanol (2 mL)-water (2 mL) was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (64 mg, 69%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f1c25d3f65eb4d248bc7073fbd2b413c
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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