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Iodine → tert-butyl(1-(5-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)cyclopropyl)methylcarbamate

HRID 1427654
Notes
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Reaction equation

HRID 1427654 reaction equation
CCN(CC)CC.II.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:29]([O:33][C:34](=[O:63])[NH:35][CH2:36][C:37]1([C:40]([NH:42][NH:43][C:44]([CH:46]2[CH2:52][CH2:51][C@@H:50]3[CH2:53][N:47]2[C:48](=[O:62])[N:49]3[O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=O)=[O:41])[CH2:39][CH2:38]1)([CH3:32])([CH3:31])[CH3:30]>C(Cl)Cl>[CH2:55]([O:54][N:49]1[C:48](=[O:62])[N:47]2[CH2:53][C@H:50]1[CH2:51][CH2:52][CH:46]2[C:44]1[O:41][C:40]([C:37]2([CH2:36][NH:35][C:34](=[O:63])[O:33][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:38][CH2:39]2)=[N:42][N:43]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 131732351tert-butyl(1-(2-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)cyclopropyl)methylcarbamate

Product 1

HCID 86701028tert-butyl(1-(5-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)cyclopropyl)methylcarbamate
Yield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et3N (8.3 g, 0.082 mol) was added to a 0° C. solution of I2 (10.43 g, 0.041 mol), PPh3 (10.76 g, 0.041 mol) in CH2Cl2 (250 mL). The mixture was allowed to warm to rt. After stirring at rt for 0.5 hr, tert-butyl(1-(2-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)cyclopropyl)methylcarbamate (10 g, 0.0205 mol) was added. The mixture was stirred at rt for another 1 hr. The mixture was concentrated, EtOAc (250 mL) was added, and the mixture was filtered to remove Ph3PO. The filtrate was concentrated and the residue was purified by silica gel column chromatography (gradient elution 33˜50% EtOAc/petroleum ether) to afford tert-butyl (1-(5-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)cyclopropyl)methylcarbamate (8 g, 83%) as a white solid. ESI-MS (EI+, m/z): 470.3 [M+H]+.

Workup

  1. stirringThe mixture was stirred at rt for another 1 hr
  2. concentrationThe mixture was concentrated
  3. additionEtOAc (250 mL) was added
  4. filtrationthe mixture was filtered
  5. customto remove Ph3PO
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (gradient elution 33˜50% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-e16da0dcd0594a849809ee6cafffd0fb
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933233B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes