tert-Butanol → HCID 67490940, compound

HRID 1917351Notes

Reaction equation

HRID 1917351 reaction equation
C(OC([C@@:8]12[CH2:15][CH2:14][C@H:13]([F:16])[C@@H:12]1[CH2:11][N:10]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:9]2)=O)(C)(C)C.FC(F)(F)[C:29]([OH:31])=[O:30].C([N:36](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:58](O)([CH3:61])([CH3:60])[CH3:59]>ClCCl>[CH2:20]([O:19][C:17]([N:10]1[CH2:11][C@@H:12]2[C@@:8]([NH:36][C:29]([O:31][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:30])([CH2:15][CH2:14][C@@H:13]2[F:16])[CH2:9]1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67490841HCID 67490841, compound

Product 1

HCID 67490940HCID 67490940, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{(1S,5S,6S)-3-Benzyloxycarbonyl-6-fluoro-3-azabicyclo[3,3,0]octan-1-yl}carboxylic acid tert-butyl ester (354 mg, 0.97 mmol) was dissolved in dichloromethane (10 mL). Trifluoroacetic acid (3 mL) was added, and the mixture was stirred for 21 hours. The solvent was evaporated under reduced pressure. A 1N sodium hydroxide solution was added to the resulting residue, and the mixture was washed with chloroform. The aqueous layer was made acidic with a hydrochloric acid solution, followed by extraction with chloroform. The extract was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the resulting residue was dissolved in toluene (8 mL). Triethylamine (197 mg, 1.95 mmol) and diphenylphosphoryl azide (359 mg, 1.27 mmol) were added in a nitrogen atmosphere, and the mixture was stirred for one hour. Thereafter, tert-butanol (8 mL) was added, and the mixture was stirred at 100° C. for 19 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (25% ethyl acetate/hexane) to give 136 mg of the title compound as a colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionA 1N sodium hydroxide solution was added to the resulting residue
  3. washthe mixture was washed with chloroform
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. dissolutionthe resulting residue was dissolved in toluene (8 mL)
  9. stirringthe mixture was stirred for one hour
  10. stirringthe mixture was stirred at 100° C. for 19 hours
  11. concentrationThe reaction solution was concentrated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-150f923e26ba48999f4924127d2fe909
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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