Acetyl chloride → HCID 58844593, compound

HRID 1271111Notes

Reaction equation

HRID 1271111 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:14][C@H:13]3[N:10]([C:11](=[O:18])[C@@H:12]3[C@H:15]([OH:17])[CH3:16])[C:9]=2[C:19]([O:21][CH2:22][O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[O:20])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:39](Cl)(=[O:41])[CH3:40]>ClCCl>[C:39]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:14][C@H:13]3[N:10]([C:11](=[O:18])[C@@H:12]3[C@H:15]([OH:17])[CH3:16])[C:9]=2[C:19]([O:21][CH2:22][O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[O:20])=[CH:4][CH:3]=1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 58844186HCID 58844186, compound

Product 1

HCID 58844593HCID 58844593, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of [(2,2-dimethylpropanoyl)oxy]methyl (5R,6S)-3-(4-aminophenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate prepared by example 26, diisopropylethylamine and dichloromethane was cooled at 0° C., and thereto was dropped acetyl chloride. After stirring, the reaction mixture was poured into ice water. The mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution in the order, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a crude product. The crude product was purified by silica gel chromatography, to give [(2,2-dimethylpropanoyl)oxymethyl (5R,6S)-3-[4-(acetylamino)phenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  3. dry with materiala saturated aqueous sodium chloride solution in the order, and dried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto give a crude product
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-983067c183714e509c0cbd707b538b3c
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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