Triethylamine → HCID 86640952, compound

HRID 1957971Notes

Reaction equation

HRID 1957971 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:17]=1)[C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.[CH3:41][NH:42][O:43][CH3:44]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:10]=[C:11]([C:12](=[O:14])[N:42]([O:43][CH3:44])[CH3:41])[CH:15]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:17]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 68423785HCID 68423785, compound

Product 1

HCID 86640952HCID 86640952, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Tert-butoxycarbonylamino-5-(methylsulfonyl)-benzoic acid (850 mg; 2.695 mmol) was diluted in 30 ml of THF, 1,1′-carbonyldiimidazole (1.3 g; 8.086 mmol) and triethylamine (0.818 ml; 5.661 mmol) were added. The reaction mixture was stirred at room temperature for 30 min., then, N,O-dimethylhydroxylamine (0.329 g; 0.005 mol) was added. The reaction mixture was refluxed overnight. Then, it was concentrated in vacuo. The crude was diluted with dichloromethane and to washed with a saturated sodium bicarbonate solution. The organic phase was separated, dried on MgSO4 and concentrated in vacuo. The crude was treated with isopropyl ether/ethyl acetate 2/1. The precipitate formed was filtered and dried in vacuo. 460 mg (1.25 mmol; 46% yield) of [3-methanesulfonyl-5-(methoxy-methyl-carbamoyl)-phenyl]-carbamic acid tert-butyl ester were obtained as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationThen, it was concentrated in vacuo
  3. additionThe crude was diluted with dichloromethane
  4. washto washed with a saturated sodium bicarbonate solution
  5. customThe organic phase was separated
  6. customdried on MgSO4
  7. concentrationconcentrated in vacuo
  8. additionThe crude was treated with isopropyl ether/ethyl acetate 2/1
  9. customThe precipitate formed
  10. filtrationwas filtered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-a93340d7f53a4026948defbcd7c99cd4
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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