Triethylamine → HCID 57794593, compound

HRID 2099778Notes

Reaction equation

HRID 2099778 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([CH2:11][C:12]1[CH:20]=[C:19]([CH3:21])[C:18]2[C:14](=[CH:15][N:16]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:17]=2)[CH:13]=1)[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CS(C)=O.CO>[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([CH2:11][C:12]1[CH:20]=[C:19]([CH3:21])[C:18]2[C:14](=[CH:15][N:16]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:17]=2)[CH:13]=1)[CH:9]=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 57794656HCID 57794656, compound

Product 1

HCID 57794593HCID 57794593, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 887MethanolSolvent2×

Conditions

Temperature
5 °C

Procedure

tert-Buty-1-hydroxy-3-(7-methyl-2-[{2-[trimethylsilyl]ethoxy}methyl]-2H-indazol-5-yl)propan-2-ylcarbamate (0.3 g, 0.69 mmol) was dissolved in anhydrous dimethyl sulfoxide (2.5 mL). Triethylamine (0.29 mL, 2.07 mmol) was then added and the reaction mixture cooled to ca. 5° C. using an ice bath. A solution of sulfur trioxide pyridine complex (0.33 g, 2.07 mmol) in dimethyl sulfoxide (2 mL) was added in one portion. After 1 min, the ice bath was removed and the reaction mixture stirred at room temperature for 20 min. The reaction mixture was poured into an ice slurry and extracted with ethyl acetate (3×). The combined organic extracts were washed with 10% citric acid (2×), water (2×), 5% sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography afforded 0.2 g (74%). Mass spec. (in methanol): 466.25 (M+MeOH+H)+.

Workup

  1. customthe ice bath was removed
  2. additionThe reaction mixture was poured into an ice slurry
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic extracts were washed with 10% citric acid (2×), water (2×), 5% sodium bicarbonate (2×), brine (2×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customColumn chromatography afforded 0.2 g (74%)

Sources & evidence

ORD record
ord-6f73a0e2447f4be9a3286a56f8ef7f8f
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

Loading…