Acetyl chloride → HCID 86752084, compound

HRID 862399Notes

Reaction equation

HRID 862399 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[Si:12]([O:19][C@@H:20]([C@H:22]1[C:30](=[O:31])[N:29]2[C@@H:23]1[CH2:24][C:25](=[O:45])[CH2:26][CH:27]=[C:28]2[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33])[CH3:21])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>ClCCl>[C:8]([O:45][C:25]1[CH2:24][C@H:23]2[N:29]([C:30](=[O:31])[C@@H:22]2[C@H:20]([O:19][Si:12]([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13])[CH3:21])[C:28]([C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=2)=[O:33])=[CH:27][CH:26]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86752085HCID 86752085, compound

Product 1

HCID 86752084HCID 86752084, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.1 ml, 7.5 mmol) followed by acetyl chloride (0.295 ml, 4.1 mmol) were added to a solution of 4-nitrobenzyl (7R,8S)-8-[(1R)-1-(tert-butyldimethylsilyloxy)-ethyl]-5,9-dioxo-1-azabicyclo[5.2.0]non-2-ene-2-carboxylate (1.67 g, 3.4 mmol) in anhydrous dichloromethane (220 ml) cooled with an ice bath. After 5 minutes, the reaction mixture was washed with water and dried over magnesium sulphate. The solvent was evaporated and the residue purified by flash chromatography, eluting with dichloromethane/ethyl acetate (95:5) to give 4-nitrobenzyl (7R,8S)-5-acetoxy-8-[(1R)-1-(tertbutyldimethyl-silyloxy)ethyl]-9-oxo-1-azabicyclo[5.2.0]non-2,4-diene-2-carboxylate (1.4 g, 77%).

Workup

  1. temperaturecooled with an ice bath
  2. washthe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was evaporated
  5. customthe residue purified by flash chromatography
  6. washeluting with dichloromethane/ethyl acetate (95:5)

Sources & evidence

ORD record
ord-b7ab6712e0d5409c99b125e7ac6850b4
Source dataset
uspto-grants-1998_02
Patent number
US05719139

Reaction notes

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