Acetyl chloride → HCID 59625453, compound

HRID 2192809Notes

Reaction equation

HRID 2192809 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH:12]1[CH2:17][CH:16]([CH2:18][OH:19])[CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[C:38]([O:19][CH2:18][CH:16]1[CH2:17][CH:12]([N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:13][N:14]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:15]1)(=[O:40])[CH3:39]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59625498HCID 59625498, compound

Product 1

HCID 59625453HCID 59625453, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl 3-{[(benzyloxy)carbonyl](2-methylpropyl)amino}-5-(hydroxymethyl)piperidine-1-carboxylate (4.6 g) and triethylamine (2.3 ml) in ethyl acetate (25 ml) was added acetyl chloride (0.94 ml) under ice-cooling, and the mixture was stirred at room temperature for 5 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the object compound (5.09 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8aa9d0b0d4274ab3989e42760072fb4c
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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