1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate → HCID 18376035, compound

HRID 2300187Notes

Reaction equation

HRID 2300187 reaction equation
C(OC([NH:8]OS(C1C(C)=CC(C)=CC=1C)(=O)=O)=O)(C)(C)C.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=O)[CH2:30][C:31]2[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][N:32]=2)=[CH:25][CH:24]=1>C(O)(C(F)(F)F)=O>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:30]=[C:31]3[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][N:32]3[N:8]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 3592851,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamateHCID 18376029HCID 18376029, compound

Product 1

HCID 18376035HCID 18376035, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Solid t-butoxycarbonyl-O-mesitylenesulfonylhydroxylamine (13.0 g 41.8 mmol)1 was added portionwise with stirring to TFA (40 ml) over 10 min then stirred for a further 30 minutes. The solution was poured onto ice (250 ml) and left until the ice melted. The resulting white solid was filtered off, washed with water, and dissolved in DCM (300 ml). The solution was dried over 4 Å mol. sieves for 1.5 hours, filtered and 6-[2-(4-fluorophenyl)-2-oxoethyl]nicotinonitrile (3.32 g 13.8 mmol) was added. The reaction was stirred at room temperature for 4 days, washed with water (100 ml), dried and purified by column chromatography. Elution with cyclohexane/ethyl acetate (3:1) gave the title compound as a yellow solid (0.6 g 18%). NMR: (CDCl3): δ 6.87 (1H, s) 7.15-7.20 (3H, m) 7.57 (1H, dd) 7.95 (2H, m) 8.84 (1H, d). Ref 1 Josef G Krause, Synthesis, 1972, 140.

Workup

  1. additionThe solution was poured onto ice (250 ml)
  2. filtrationThe resulting white solid was filtered off
  3. washwashed with water
  4. dissolutiondissolved in DCM (300 ml)
  5. customThe solution was dried over 4 Å mol
  6. waitsieves for 1.5 hours
  7. filtrationfiltered
  8. stirringThe reaction was stirred at room temperature for 4 days
  9. washwashed with water (100 ml)
  10. customdried
  11. custompurified by column chromatography
  12. washElution with cyclohexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-54d8dcdda52d4a07a895dd74f77345d9
Source dataset
uspto-grants-2002_12
Patent number
US06498166B1

Reaction notes

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