tert-Butanol → HCID 67192130, compound

HRID 2359649Notes

Reaction equation

HRID 2359649 reaction equation
CC[N:3]([CH2:6]C)CC.[C:8]([C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][CH:31]=1)[O:13][C:14]1[C:19](C(O)=O)=[CH:18][N:17]=[C:16]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[N:15]=1)#[N:9].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1.[CH3:49][C:50]([OH:53])([CH3:52])[CH3:51]>>[C:50]([O:53][C:6](=[O:39])[NH:3][C:19]1[C:14]([O:13][C:12]2[CH:29]=[CH:30][CH:31]=[C:10]([C:8]#[N:9])[CH:11]=2)=[N:15][C:16]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[N:17][CH:18]=1)([CH3:52])([CH3:51])[CH3:49]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67190775HCID 67190775, compound

Product 1

HCID 67192130HCID 67192130, compound

Procedure

To a solution of Et3N (0.058 mL; 0.42 mmol) in tBuOH (9.35 mL) was added 4 Å molecular sieves (3 g) and the mixture was refluxed for 30 min under a N2 atmosphere. Compound 14f (0.1 g; 0.31 mmol) and diphenylphosphorylazide (0.085 mL; 0.39 mmol) were added to the mixture and refluxed for 3 h under a N2 atmosphere. The reaction mixture was allowed to cool to room temperature, filtered and concentrated. The resulting residue was suspended in EtOAc (10 mL) and washed with water (10 mL) and brine (10 mL), dried over MgSO4 and concentrated. The crude product was purified by reverse phase HPLC to give Compound 14g. 1H NMR (300 MHz, CD3OD): δ 9.30 (s, 1H), 9.20 (s, 1H), 8.80 (d, 1H), 8.65 (d, 1H), 7.80 (dd, 1H), 7.70 (s, 1H), 7.65 (m, 3H), 1.50 (s, 9H); MS: m/z 390.3 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 30 min under a N2 atmosphere
  2. temperaturerefluxed for 3 h under a N2 atmosphere
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washwashed with water (10 mL) and brine (10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c753b4d135834f09ad31aacb06e4e7e2
Source dataset
uspto-grants-2014_04
Patent number
US08685990B2

Reaction notes

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