Acetyl chloride → HCID 131732940, compound

HRID 2171276Notes

Reaction equation

HRID 2171276 reaction equation
C(=O)([O-])O.[Na+].[C:6](Cl)(=[O:8])[CH3:7].C1COCC1.O.[O:16]=[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[N:18]1[CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH:28]1[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37]>C(OCC)(=O)C>[C:6]([N:30]1[CH2:31][CH2:32][CH:27]([N:18]2[C:17](=[O:16])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:26])[CH:28]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH2:29]1)(=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 21881883Oxolane--water (1/1)HCID 131732939HCID 131732939, compound

Product 1

HCID 131732940HCID 131732940, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydrogen carbonate (341 mg) and acetyl chloride (0.086 ml) were added to a THF/water (2 ml/2 ml) solution containing tert-butyl (4-(1,3-dioxoisoindolin-2-yl)piperidin-3-yl)carbamate (280 mg) obtained in the 2nd step under ice cooling, followed by stirring at room temperature for 0.5 hours. Ethyl acetate was added to the reaction solution. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. Next, the solvent was distilled away under reduced pressure. A white solid of tert-butyl (1-acetyl-4-(1,3-dioxoisoindolin-2-yl)piperidin-3-yl)carbamate (301 mg) was thus obtained.

Workup

  1. customobtained in the 2nd step under ice cooling
  2. washThe organic layers were washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationNext, the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-811ce098e8ad47578eaa6cb5d2907c2d
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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