Acetyl chloride → HCID 11219404, compound

HRID 1374424Notes

Reaction equation

HRID 1374424 reaction equation
C(Cl)(=O)C.[CH3:5][O:6][CH2:7][C@@H:8]1[CH2:13][C:12]([C:14]([O:16][C:17](C)(C)C)=[O:15])=[CH:11][CH2:10][N:9]1[C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22]>CO>[CH3:5][O:6][CH2:7][C@@H:8]1[CH2:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH2:10][N:9]1[C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86592523HCID 86592523, compound

Product 1

HCID 11219404HCID 11219404, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To methanol (19 ml, 470 mmol) was added at 0° C. acetyl chloride (12 ml, 169 mmol) and the mixture was stirred at the same temperature for 30 minutes. This solution was added to a solution of 1-allyl 4-tert-butyl (2S)-2-(methoxymethyl)-3,6-dihydro-1,4(2 H)-pyridinedicarboxylate (744 mg, 2.4 mmol) in methanol (3 ml) and the mixture was stirred at room temperature for 2 hours. The solvent was removed and the residue was dissolved in ethyl acetate. The solution was washed with a saturated sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo to give 1-allyl 4-methyl (2S)-2-(methoxymethyl)-3,6-dihydro-1,4(2 H)-pyridinedicarboxylate (600 mg, 93%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with a saturated sodium hydrogen carbonate solution
  5. dry with materiala saturated aqueous sodium chloride solution and dried over magnesium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4fead3326e1a4502ad60b933eec1a087
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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