Tributylstannane → HCID 68765971, compound

HRID 351393Notes

Reaction equation

HRID 351393 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:14](=[O:15])[C@@H:13]2[CH2:16][C@@H:9]1[C@@H:10](I)[CH2:11][C@@H:12]2[NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[SnH](CCCC)CCCC>C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>[C:1]([O:5][C:6]([N:8]1[C:14](=[O:15])[C@@H:13]2[CH2:16][C@H:9]1[CH2:10][CH2:11][C@@H:12]2[NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 68766763(1R,2S,4S,5R)-2-benzyloxycarbonylamino-4-iodo-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester

Product 1

HCID 68765971HCID 68765971, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 241BenzeneSolvent

Procedure

A sample of (1R,2S,4S,5R)-2-benzyloxycarbonylamino-4-iodo-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester (43.3 g) was dissolved in benzene (580 mL) prior to the addition of Bu3SnH (27.8 g) and AIBN (0.7 g). The resulting mixture was warmed to a gentle reflux for 3 h. After cooling, the solvent was removed and hexane was added. The resulting white solid was collected by vacuum filtration to give (1R,2S,5R)-2-benzyloxycarbonylamino-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester (29.5 g). MS found: (M+Na)+=397.4.

Workup

  1. temperatureThe resulting mixture was warmed to
  2. temperaturea gentle reflux for 3 h
  3. temperatureAfter cooling
  4. customthe solvent was removed
  5. additionhexane was added
  6. filtrationThe resulting white solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-3cb287ee2c27488c859ab1729a79989f
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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