Acetyl chloride → HCID 20533759, compound

HRID 1156731Notes

Reaction equation

HRID 1156731 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH2:10][S:11][C:12]1[CH2:18][CH:17]2[N:14]([C:15](=[O:21])[CH:16]2[CH2:19][CH3:20])[C:13]=1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:23].[C:35](Cl)(=[O:37])[CH3:36]>ClCCl.C1C=CC=CC=1>[C:35]([O:8][CH2:9][CH2:10][S:11][C:12]1[CH2:18][CH:17]2[N:14]([C:15](=[O:21])[CH:16]2[CH2:19][CH3:20])[C:13]=1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:23])(=[O:37])[CH3:36]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 12961587HCID 12961587, compound

Product 1

HCID 20533759HCID 20533759, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (13.3 microliters) was added to a solution in 2 ml of dichloromethane of 3.75 mg of the p-nitrobenzyl 3-(2-hydroxyethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate obtained in Example 44. Then, 6.8 microliters of acetyl chloride was added dropwise to the resulting solution at -10° C. with stirring. At the same temperature, the mixture was stirred for 10 minutes. The reaction mixture was diluted with 10 ml of benzene, and washed three times with 5 ml of a 0.1 M phosphate buffer (pH6.8). The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to afford a yellow oily product.

Workup

  1. stirringAt the same temperature, the mixture was stirred for 10 minutes
  2. washwashed three times with 5 ml of a 0.1 M phosphate buffer (pH6.8)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto afford a yellow oily product

Sources & evidence

ORD record
ord-c5be0b8c469547c9855eb1115d5fa6b1
Source dataset
uspto-grants-1982_06
Patent number
US04337199

Reaction notes

Loading…