Acetyl chloride → HCID 54334358, compound

HRID 622592Notes

Reaction equation

HRID 622592 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][O:12][N:13]=[CH:14][C:15]([NH:17][C@H:18]2[C@@H:21]([S:22][CH2:23][CH2:24][OH:25])[NH:20][C:19]2=[O:26])=[O:16])[N:10]=1)=[O:4].[CH2:27]1[O:30][CH:28]1C.C(Cl)(=O)C>CC(N(C)C)=O>[C:28]([O:25][CH2:24][CH2:23][S:22][C@H:21]1[NH:20][C:19](=[O:26])[C@H:18]1[NH:17][C:15](=[O:16])[CH:14]=[N:13][O:12][CH2:11][C:9]1[N:10]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][Cl:1])[S:7][CH:8]=1)(=[O:30])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 6378Propylene OxideHCID 53712198HCID 53712198, compound

Product 1

HCID 54334358HCID 54334358, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.65 g of (3R,4R)-3-[[[(2-chloroacetylamino-4-thiazolyl)(methoxyimino)]acetyl]amino]-4-[[2-(hydroxy)ethyl]thio]-2-azetidinone in 5 ml of dimethylacetamide are added 1 ml of propylene oxide and 0.36 g of acetyl chloride, and the mixture is stirred at 0° C. for 3 hours. After further addition of 0.36 g of acetyl chloride, the mixture is stirred for additional 3 hours. The solvent is then distilled off under reduced pressure to give crystals, which are collected by filtration and washed with methylene chloride. The above procedure gives 0.558 g of (3R,4R)-4-[[2-(acetoxy)ethyl]thio]-3-[[[(2-chloroacetylamino-4-thiazolyl)(methoxyimino)]acetyl]amino]-2-azetidinone.

Workup

  1. stirringthe mixture is stirred for additional 3 hours
  2. distillationThe solvent is then distilled off under reduced pressure
  3. customto give crystals, which
  4. filtrationare collected by filtration
  5. washwashed with methylene chloride

Sources & evidence

ORD record
ord-d1dfb4b860f746ba936f47c553bb3d96
Source dataset
uspto-grants-1988_09
Patent number
US04771045

Reaction notes

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