Potassium Carbonate → HCID 21772276, compound

HRID 1277707Notes

Reaction equation

HRID 1277707 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:22])[C@H:12]2[C@@H:15](OS(C)(=O)=O)[CH3:16])[C:9]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:22])/[C:12]/2=[CH:15]/[CH3:16])[C:9]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53730686HCID 53730686, compound

Product 1

HCID 21772276HCID 21772276, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

p-Nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-[(S)-1-methylsulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e11) (67 mg) was stirred with K2CO3 (70 mg) in dimethylformamide (2 ml) at room temperature for 1 hour. Work-up as in Example 2 gave a residue which was triturated with ethyl acetate/ether to afford a solid which was collected by filtration. The solid (10 mg) was identified as p-nitrobenzyl (5R,6E)-3-(2-acetamidoethylthio)-6-ethylidene-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e12); δ(DMF-d7) ca. 1.85 (3H, d, CH3CH), 1.87 (3H, s, CH3CO) ca. 2.7-3.5 (6H, m, NCH2CH2S and 4-CH2), 4.85 (1H, br t, J 9 Hz, 5-CH), 5.29 and 5.53 (each 1H, d, J 14 Hz, CH2Ar), 6.38 (1H, br q, J 7 Hz, CH3CH), 7.76 and 8.20 (each 2H, d, J 9 Hz, ArCH2), and ca. 8.0 (1H, NH).

Workup

  1. customgave a residue which
  2. customwas triturated with ethyl acetate/ether
  3. customto afford a solid which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b177c018f79e49b08582c6db76d33b9b
Source dataset
uspto-grants-1981_07
Patent number
US04278686

Reaction notes

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