Iodine → HCID 86701004, compound

HRID 1855165Notes

Reaction equation

HRID 1855165 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.II.[CH2:22]([O:29][N:30]1[C:36](=[O:37])[N:35]2[CH2:38][C@H:31]1[CH2:32][CH2:33][C@H:34]2[C:39]([NH:41][NH:42][C:43](=O)[CH2:44][CH2:45][CH2:46][NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:40])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][N:30]1[C:36](=[O:37])[N:35]2[CH2:38][C@H:31]1[CH2:32][CH2:33][C@H:34]2[C:39]1[O:40][C:43]([CH2:44][CH2:45][CH2:46][NH:47][C:48](=[O:54])[O:49][C:50]([CH3:52])([CH3:53])[CH3:51])=[N:42][N:41]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 807Iodine2×HCID 11776TriphenylphosphineHCID 86701003HCID 86701003, compound

Product 1

HCID 86701004HCID 86701004, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To s solution of PPh3 (2.6 g, 10.0 mmol) in dry DCM (60 mL) was added I2 (2.6 g, 10.0 mmol). After I2 was dissolved completely, TEA (3.5 mL, 25.0 mmol) was added quickly at rt. The mixture was stirred for 15 mins. Tert-butyl 4-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinyl)-4-oxobutylcarbamate (2.4 g, 5.0 mmol) was added. The mixture was stirred at rt for 1 hr. The solvent was concentrated. EtOAc (250 mL) was added, and the solution was filtrated to remove POPh3. The filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (gradient elution 0˜40% EtOAc/petroleum ether) to afford tert-butyl 3-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)propylcarbamate (2.0 g, 86%) as a white solid. ESI-MS (EI+, m/z): 458 [M+H]+.

Workup

  1. stirringThe mixture was stirred at rt for 1 hr
  2. concentrationThe solvent was concentrated
  3. additionEtOAc (250 mL) was added
  4. filtrationthe solution was filtrated
  5. customto remove POPh3
  6. concentrationThe filtrate was concentrated
  7. customThe resulting residue was purified by silica gel column chromatography (gradient elution 0˜40% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-38fbb87bf46c4e8e90684104956b7169
Source dataset
uspto-grants-2015_02
Patent number
US08962843B2

Reaction notes

Loading…