tert-Butanol → HCID 21837517, compound

HRID 1739792Notes

Reaction equation

HRID 1739792 reaction equation
C([N:3]([CH2:6]C)[CH2:4][CH3:5])C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[S:25]1[C:34]2[C:29](=[CH:30][CH:31]=CC=2C(O)=O)[CH2:28][CH2:27][CH2:26]1.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>C1(C)C=CC=CC=1>[C:38]([O:42][C:6]([NH:3][C:4]1[CH:5]=[CH:31][CH:30]=[C:29]2[C:34]=1[S:25][CH2:26][CH2:27][CH2:28]2)=[O:15])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 23291416HCID 23291416, compound

Product 1

HCID 21837517HCID 21837517, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

At room temperature, 9.0 ml (64.4 mmol) of triethylamine, then 13.9 ml (64.4 mmol) of diphenylphosphoryl azide are added to 10 g (51.5 mmol) of thiochroman-8-carboxylic acid in 260 ml of toluene. The whole is heated at 90° C. for 2 hours, then 4.8 g (64.4 mmol) of tert-butanol dissolved in 10 ml of toluene are added dropwise and the temperature is subsequently maintained at 90° C. for a further 20 hours. The whole is allowed to cool and washed with 120 ml of water, 120 ml of 0.N hydrochloric acid, 120 ml of water, 120 ml of a saturated aqueous sodium hydrogen carbonate solution and 120 ml of water. After drying over magnesium sulphate and evaporation, the residue is taken up in cyclohexane and triturated, and a solid is removed by filtration; the filtrate is concentrated (13.3 g ) and then chromatographed on 1 kg of silica (eluant: dichloromethane) to yield 11.2 g of the desired product (yield: 82%).

Workup

  1. additionare added dropwise
  2. temperaturethe temperature is subsequently maintained at 90° C. for a further 20 hours
  3. temperatureto cool
  4. washwashed with 120 ml of water, 120 ml of 0.N hydrochloric acid, 120 ml of water, 120 ml of a saturated aqueous sodium hydrogen carbonate solution and 120 ml of water
  5. dry with materialAfter drying over magnesium sulphate and evaporation
  6. customtriturated
  7. customa solid is removed by filtration
  8. concentrationthe filtrate is concentrated (13.3 g )
  9. customchromatographed on 1 kg of silica (eluant: dichloromethane)

Sources & evidence

ORD record
ord-97d3f23eeaa5454fb34690727c30317f
Source dataset
uspto-grants-1999_10
Patent number
US05968954

Reaction notes

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