Iodine → HCID 86701038, compound

HRID 1427598Notes

Reaction equation

HRID 1427598 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][C:45]1([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:47][CH2:46]1)=[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][C:45]2([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:52])([CH3:53])[CH3:54])[CH2:47][CH2:46]2)=[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 86701037HCID 86701037, compound

Product 1

HCID 86701038HCID 86701038, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To s solution of PPh3 (5.2 g, 20.0 mmol) in dry DCM (60 mL) was added I2 (5.1 g, 20.0 mmol). After I2 was dissolved completely, TEA (7.0 mL, 50.0 mmol) was added quickly at rt. The mixture was stirred for 15 mins. Tert-butyl 1-(2-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinyl)-2-oxoethyl)cyclopropyl-carbamate (4.9 g, 10.0 mmol) was added and the mixture was stirred at rt for 1 hr. The solvent was concentrated. EtOAc (250 mL) was added, and the solution was filtered to remove PPh3O. The filtrate was concentrated and the residue was purified by silica gel column chromatography (0˜60% gradient elution EtOAc/petroleum ether) to afford tert-butyl 1-((5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)methyl)cyclopropyl-carbamate (4.1 g, 87%) as a white solid. ESI-MS (EI+, m/z): 470 [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 filtered
  5. customto remove PPh3O
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (0˜60% gradient elution EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-79109d0c2dc2417499ebbce4338b0db5
Source dataset
uspto-grants-2015_01
Patent number
US08933232B2

Reaction notes

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