Triethylamine → 7-N-(tert-Butoxycarbonyl)-8-(methanesulfonyloxymethyl)-2-(trifluoromethyl) 5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

HRID 133078Notes

Reaction equation

HRID 133078 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=[C:10]2[CH:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]([F:18])([F:20])[F:19])[N:16]=[C:10]2[CH:9]1[CH2:21][O:22][S:31]([CH3:30])(=[O:33])=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 693626567-N-(tert-Butoxycarbonyl)-8-(hydroxymethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

Product 1

HCID 877981657-N-(tert-Butoxycarbonyl)-8-(methanesulfonyloxymethyl)-2-(trifluoromethyl) 5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 100 mg (0.31 mmol) of 7-N-(tert-butoxycarbonyl)-8-(hydroxymethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-α]pyrazine in 1.0 mL of dichloromethane was added sequentially 0.047 mL (0.341 mmol) of triethylamine and 0.029 mL (0.372 mmol) of methanesulfonyl chloride. The reaction mixture was stirred at 0° C. and allowed to warm to room temperature for 4 h. Aqueous sodium bicarbonate solution was added, and the resultant mixture was extracted with three portions of dichloromethane. The combined organics were washed with brine, dried over magnesium sulfate, and concentrated to give a yellow oil which was used without further purification. LC/MS 401 (M+1).

Workup

  1. temperatureto warm to room temperature for 4 h
  2. extractionthe resultant mixture was extracted with three portions of dichloromethane
  3. washThe combined organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a yellow oil which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-0d7e65152d464df687f2d3c46340653b
Source dataset
uspto-grants-2008_06
Patent number
US07390809B2

Reaction notes

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