tert-Butanol → HCID 16067576, compound

HRID 2059810Notes

Reaction equation

HRID 2059810 reaction equation
[CH:1]([N:4]([CH:25]([CH3:27])[CH3:26])[C:5](=[O:24])[CH:6]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8]C(O)=O)([CH3:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])=CC=1.CC[N:47]([CH2:50]C)CC.[CH3:52][C:53]([OH:56])([CH3:55])[CH3:54]>>[CH:1]([N:4]([CH:25]([CH3:26])[CH3:27])[C:5](=[O:24])[CH:6]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][NH:47][C:50](=[O:35])[O:56][C:53]([CH3:55])([CH3:54])[CH3:52])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 16067579HCID 16067579, compound

Product 1

HCID 16067576HCID 16067576, compound

Procedure

A suspension of 5-(diisopropylamino)-5-oxo-3-phenyl-4-pyridin-3-ylpentanoic acid (5.87 g, 15.93 mmol) and powdered molecular sieves (4 A) in t-BuOH (200 mL) was stirred at room temperature for 10 min under argon. To this mixture was then added DPPA (4.12 mL, 19.1 mmol) followed by Et3N (2.66 mL, 19.1 mmol), and the reaction mixture was heated at reflux temperature. After 25 h, it was cooled down to rt, filtered through a pad of celite (washing with CH2Cl2). The combined filtrate and washings were concentrated. The residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. Purification by flash chromatography using a linear gradient of 0% to 5% MeOH—NH4OH (90:10 v/v) in CH2Cl2 gave a pale yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature
  3. waitAfter 25 h
  4. temperatureit was cooled down to rt
  5. filtrationfiltered through a pad of celite (washing with CH2Cl2)
  6. concentrationThe combined filtrate and washings were concentrated
  7. customThe residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3
  8. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  9. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  10. concentrationconcentrated
  11. customPurification by flash chromatography
  12. customgave a pale yellow solid

Sources & evidence

ORD record
ord-f890b59b85284c478846ae0fa7eb32ab
Source dataset
uspto-grants-2012_10
Patent number
US08278317B2

Reaction notes

Loading…