1,5-Diazabicyclo(5,4,0)undec-5-ene → HCID 86737866, compound

HRID 1277713Notes

Reaction equation

HRID 1277713 reaction equation
[C:1]([NH:4]/[CH:5]=[CH: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][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])(=[O:3])[CH3:2].N12CCCCC1C=NCCC2>ClCCl>[C:1]([NH:4]/[CH:5]=[CH: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][Si:26]([C:39]([CH3:40])([CH3:42])[CH3:41])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:24])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 86737867HCID 86737867, compound

Product 1

HCID 86737866HCID 86737866, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

tert-Butyldiphenylsilyl (5R,6S)-3-[(E)-2-acetamidoethenylthio]-6-[(1S)-1-methylsulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (20 mg) in dichloromethane (1 ml) was treated with 1,5-diazabicyclo[5.4.0]undec-5-ene (0.05 ml of a 100 mg/ml solution in CH2Cl2) at room temperature for 20 min. The dichloromethane solution was diluted, washed with water, dried (MgSO4) and evaporated in vacuo to give tert-Butyldiphenylsilyl (5R)-3-[(E)-2-acetamidoethenylthio]-6-[(Z)-ethylidene]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e67) (6.8 mg). νmax 1770, 1700, 1675, 1640, 1620 cm-1. δ(CDCl3 +D2O) 1.11[9H,s,C(CH3)3 ], 1.85 (3H,s,CH3CO), 2.05 (3H,d,J approx. 7 Hz, CH3CH), 3.7-3.3 (2H,m, 4--CH2), 4.4-4.7 (1 H,m, 5--CH), 5.65 (1H,d,J 14 Hz, SCH=CH), 5.83 (1H, broadened q, J ca 7 Hz, CH3CH), 7.00 (1H,d,J 14 Hz CHNH), 7.2-7.8 (10H,m,Ar--H).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-fdc707f5681045539dca6018da41c068
Source dataset
uspto-grants-1981_07
Patent number
US04278686

Reaction notes

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