Bromotrichloromethane → HCID 58243993, compound

HRID 389144Notes

Reaction equation

HRID 389144 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][C:19]([CH3:37])([C:21]2[N:25]([CH3:26])[C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:36])([F:35])[F:34])=[N:23][N:22]=2)[CH3:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11]O)=[O:8].COCCN(CCOC)S(F)(F)F.BrC(Cl)(Cl)Cl.C1CCN2C(=NCCC2)CC1>C(OCC)(=O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][C:19]([CH3:20])([C:21]2[N:25]([CH3:26])[C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:36])([F:35])[F:34])=[N:23][N:22]=2)[CH3:37])=[C:6]([C:7]2[O:8][CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[N:9]=2)[CH:17]=1

Participants

7

Reactant 4

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58243700HCID 58243700, compound

Product 1

HCID 58243993HCID 58243993, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl N-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzoyl]-L-serinate (1.41 g) was mixed with dichloromethane (45 ml), followed by cooling to −78° C. under a nitrogen atmosphere. 2-methoxy-N-(2-methoxyethyl)-N-(trifluoro-λ4-sulfanyl)ethanamine (0.580 ml) was added thereto, followed by stirring for 2 hours, and bromo(trichloro)methane (0.920 ml) and DBU (1.40 ml) were sequentially added thereto at 0° C., followed by stirring for 3 hours. The reaction solution was diluted with ethyl acetate, washed with water, saturated aqueous sodium bicarbonate solution and then saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:1). The resulting solid was washed with diisopropylether to obtain, as a white solid, methyl 2-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,3-oxazole-4-carboxylate (1.05 g).

Workup

  1. customat 0° C.
  2. stirringby stirring for 3 hours
  3. washwashed with water, saturated aqueous sodium bicarbonate solution
  4. dry with materialsaturated brine in this order, and dried over anhydrous magnesium sulfate
  5. customthe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:1)
  7. washThe resulting solid was washed with diisopropylether

Sources & evidence

ORD record
ord-1a0086e4fe97477bae9d32e731452c28
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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