Iodine → HCID 86701022, compound

HRID 1427648Notes

Reaction equation

HRID 1427648 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.II.[C:22]([O:26][C:27](=[O:55])[N:28]([CH2:30][CH2:31][C:32]([NH:34][NH:35][C:36]([C@@H:38]1[CH2:44][CH2:43][C@@H:42]2[CH2:45][N:39]1[C:40](=[O:54])[N:41]2[O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=O)=[O:33])[CH3:29])([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[CH2:47]([O:46][N:41]1[C:40](=[O:54])[N:39]2[CH2:45][C@H:42]1[CH2:43][CH2:44][C@H:38]2[C:36]1[O:33][C:32]([CH2:31][CH2:30][N:28]([CH3:29])[C:27](=[O:55])[O:26][C:22]([CH3:24])([CH3:25])[CH3:23])=[N:34][N:35]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 807Iodine2×HCID 11776TriphenylphosphineHCID 86701021HCID 86701021, compound

Product 1

HCID 86701022HCID 86701022, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of PPh3 (5.3 g, 20.0 mmol) in CH2Cl2 (250 mL) at rt was added I2(5.2 g, 20.0 mmol). After I2 was dissolved completely, the solution was cooled to 0° C. and TEA (7.0 mL, 50.0 mmol) was added. Tert-butyl3-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinyl)-3-oxopropyl(methyl)carbamate (4.8 g, 10.0 mol) was added and the mixture was stirred at rt for 1 hr. The mixture was concentrated, EtOAc (250 mL) was added, and the solution was filtered to remove POPh3. The filtrate was concentrated and the residue was purified by silica gel column chromatography (gradient elution 30 to 50% EtOAc/petroleum ether) to afford tert-butyl 2-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)ethyl(methyl)carbamate (4.1 g, 85%) as a white solid. ESI-MS (EI+, m/z): 458 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. additionEtOAc (250 mL) was added
  3. filtrationthe solution was filtered
  4. customto remove POPh3
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (gradient elution 30 to 50% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-7c725c81bd104a1baf2f8c0dfc2de46e
Source dataset
uspto-grants-2015_01
Patent number
US08933233B2

Reaction notes

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