Sulfur, trifluoro(N-methylmethanaminato)- → HCID 10126717, compound

HRID 1816434Notes

Reaction equation

HRID 1816434 reaction equation
CN(S(F)(F)[F:5])C.O[C:9]1([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][C@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]3=[O:33])=[CH:19][C:18]=2[F:34])[CH:14]=[CH:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]1>C(Cl)Cl.C(OCC)(=O)C>[F:34][C:18]1[CH:19]=[C:20]([N:23]2[CH2:27][C@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]2=[O:33])[CH:21]=[CH:22][C:17]=1[C:9]1([F:5])[CH:14]=[CH:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 123203Sulfur, trifluoro(N-methylmethanaminato)-HCID 10309658HCID 10309658, compound

Product 1

HCID 10126717HCID 10126717, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(N,N-Dimethylamino)sulfur trifluoride (2.5 μL, 0.019 mmol) is added to a cooled (−78° C.) solution of the product of Example 12 (6.0 mg, 0.014 mmol) in DCM (0.75 mL). The solution is warmed slowly to room temperature over 4 hours and diluted with ethyl acetate. The organic solution is extracted with satd NaHCO3, H2O, brine and dried (Na2SO4). The crude product is purified by preparative TLC (7% MeOH-DCM) to provide the title compound as a mixture of diastereomers.

Workup

  1. extractionThe organic solution is extracted with satd NaHCO3, H2O, brine
  2. dry with materialdried (Na2SO4)
  3. customThe crude product is purified by preparative TLC (7% MeOH-DCM)

Sources & evidence

ORD record
ord-03435f70ab264ae1af81bd5d8ed65ea0
Source dataset
uspto-grants-2005_04
Patent number
US06884813B2

Reaction notes

Loading…