tert-Butanol → HCID 11133043, compound

HRID 635086Notes

Reaction equation

HRID 635086 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14]([F:17])([F:16])[C@@H:13]([C:18]2(C(O)=O)[CH2:20][CH2:19]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C([N:43]([CH2:46]C)CC)C.[C:48]([OH:52])([CH3:51])([CH3:50])[CH3:49]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][C@H:13]([C:18]2([NH:43][C:46]([O:52][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:31])[CH2:19][CH2:20]2)[C:14]([F:16])([F:17])[CH2:15]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11809522HCID 11809522, compound

Product 1

HCID 11133043HCID 11133043, compoundYield 60.1%

Procedure

1-[1-Benzyloxycarbonyl-4,4-difluoro-3-(S)-pyrrolidinyl]cyclopropanecarboxylic acid (1.953 g, 6.004 mmol) was dissolved in tert-butyl alcohol (50 ml), and the solution was mixed with diphenylphosphoryl azide (1,426 μl, 6.604 mmol) and triethylamine (1,381 μl, 9.906 mmol), stirred at room temperature for 2 hours and then heated under reflux for 16 hours. The reaction solution was cooled and then concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography and eluted with an eluant of n-hexane:ethyl acetate=4:1, to thereby obtain 1.430 g (60.1%) of the title compound as a colorless oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. temperatureThe reaction solution was cooled
  4. concentrationconcentrated under reduced pressure
  5. washeluted with an eluant of n-hexane

Sources & evidence

ORD record
ord-af0a9c9d69a74cc8adc583a07ef3cd8d
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Reaction notes

Loading…