Chloroform → HCID 86588092, compound

HRID 1828414Notes

Reaction equation

HRID 1828414 reaction equation
[CH:1]1([C:5]2[N:6]=[C:7]([CH2:10][CH2:11][C:12]3[CH:40]=[CH:39][N:15]4[C:16](=[O:38])[C:17](/[CH:29]=[CH:30]/[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[C:18]([N:20]5[CH2:25][CH2:24][CH2:23][CH:22]([O:26]C=O)[CH2:21]5)[N:19]=[C:14]4[CH:13]=3)[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].C(Cl)(Cl)Cl>CO.[Cl-].[Na+].O>[CH:1]1([C:5]2[N:6]=[C:7]([CH2:10][CH2:11][C:12]3[CH:40]=[CH:39][N:15]4[C:16](=[O:38])[C:17](/[CH:29]=[CH:30]/[C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])=[C:18]([N:20]5[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]5)[N:19]=[C:14]4[CH:13]=3)[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 10942334Sodium Methoxide3×HCID 86588094HCID 86588094, compound

Product 1

HCID 86588092HCID 86588092, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

tert-Butyl (E)-3-[8-[2-(4-cyclobutyl-1,3-thiazol-2-yl)ethyl]-2-(3-formyloxy-piperidino)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoate (95 mg, 0.168 mmol) dissolved in methanol (4 ml) was added with sodium methoxide (4 mg, 0.074 mmol) under ice cooling and stirred for 45 minutes under ice cooling. Then the reaction solution was further added with sodium methoxide (4 mg), and after 5 minutes, further added with sodium methoxide (10 mg). After the reaction solution was stirred for 15 minutes, the reaction was stopped with saturated brine and added with chloroform for extraction. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure, and the residue was purified by thin layer silica gel chromatography (chloroform:methanol=20:1) to obtain 76 mg (84%) of the title compound as yellow crystals in a mixture with triphenylphosphine oxide.

Workup

  1. waitafter 5 minutes
  2. stirringAfter the reaction solution was stirred for 15 minutes
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by thin layer silica gel chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-f0aeb244381a4c47b93b3905c65087e7
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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