tert-Butanol → HCID 21084092, compound

HRID 347912Notes

Reaction equation

HRID 347912 reaction equation
C([N:3](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[O:25]=[C:26]1[N:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:30]2[S:38][C:39](C(O)=O)=[C:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:29]=2[CH:28]=[CH:27]1.[C:50]([O-:53])(O)=[O:51].[Na+].[C:55](O)([CH3:58])([CH3:57])[CH3:56]>>[O:25]=[C:26]1[N:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:30]2[S:38][C:39]([NH:3][C:50](=[O:51])[O:53][C:55]([CH3:58])([CH3:57])[CH3:56])=[C:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:29]=2[CH:28]=[CH:27]1

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 21083991HCID 21083991, compound

Product 1

HCID 21084092HCID 21084092, compoundYield 94%

Procedure

Triethylamine (0.076 mL, 0.55 mmol) and diphenylphosphoryl azide (0.119 mL, 0.55 mmol) were added to a solution of the compound of Example 59 (174 mg, 0.5 mmol) in dry tert-butanol (5 mL) and the mixture heated under reflux under nitrogen for 6 h. The cooled mixture was poured into saturated NaHCO3(aq) (20 mL) and extracted with DCM (2×20 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography on silica (EtOAc) to give the title compound (1 96 mg, 94%). δH (CDCl3) 7.5–7.25 (11H, m), 6.70 (1H, br s), 6.46 (1H, d, J 9 Hz), 1.29 (9H, s). m/z (ES+) 419 (M+H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux under nitrogen for 6 h
  3. extractionextracted with DCM (2×20 mL)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography on silica (EtOAc)

Sources & evidence

ORD record
ord-e9c6c21b205f498290156a4e1c6f2680
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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