Methyl N-(triethylammoniosulfonyl)carbamate → HCID 57675218, compound

HRID 490912Notes

Reaction equation

HRID 490912 reaction equation
CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[CH2:16]([N:18]1[C:22]2=[N:23][CH:24]=[C:25]([C:34]([NH2:36])=O)[C:26]([NH:27][CH:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[C:21]2[CH:20]=[N:19]1)[CH3:17]>C1COCC1>[CH2:16]([N:18]1[C:22]2=[N:23][CH:24]=[C:25]([C:34]#[N:36])[C:26]([NH:27][CH:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)=[C:21]2[CH:20]=[N:19]1)[CH3:17]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamate2×HCID 10424262HCID 10424262, compound

Product 1

HCID 57675218HCID 57675218, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Burgess Reagent 4.53 g, 19.0 mmol) was added to a suspension of Intermediate 136 (5.0 g, 17.3 mmol) in THF (80 ml). The reaction mixture was stirred at room temperature for 18 hours then a further portion of Burgess Reagent (0.9 g, 1.8 mmol) was added and stirring continued for 5 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was washed with water, dried and evaporated in vacuo to afford Intermediate 137 as an off-white solid (4.43 g). LCMS showed MH+=272; TRET=2.40 min

Workup

  1. stirringstirring
  2. waitcontinued for 5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between dichloromethane and water
  5. washThe organic phase was washed with water
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ba2cde1db4ae4fb792f6b702eb516df9
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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