Dichloromethane → N-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2, 4-triazol-1-yl)-2-butyl]methanesulfonamide

HRID 274612Notes

Reaction equation

HRID 274612 reaction equation
ClCCl.[NH2:4][C@H:5]([CH3:22])[C@:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])([OH:13])[CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>O>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[C@@:6]([OH:13])([CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1)[C@H:5]([NH:4][S:31]([CH3:30])(=[O:33])=[O:32])[CH3:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10967497(2R,3R)-3-Amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Product 1

HCID 18659261N-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2, 4-triazol-1-yl)-2-butyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To dichloromethane (10 ml) was added (2R,3R)-3-amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (0.54 g). To the mixture was added, under ice-cooling, triethylamine (0.28 ml), to which was added dropwise methanesulfonyl chloride (0.15 ml), followed by stirring for 15 minutes at room temperatures. To the mixture was added water (20 ml), which was subjected to extraction with dichloromethane (30 ml). The extract was washed with water (20 ml) and dried (MgSO4). Then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel chromatography (2.9×30 cm, eluent: ethyl acetate/methanol =25/1). The object fraction was concentrated to give N-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2, 4-triazol-1-yl)-2-butyl]methanesulfonamide (Compound 49, 0.52 g) as a colorless oily product. 1H-NMR(CDCl3) δ: 1.04(3H,d,J=6.6 Hz), 3.07(3H,s), 4.12-4.21(1H,m), 4.81(1H,d,J=14 Hz), 4.97(1H,d,J=14 Hz), 5.28(1H,d,J=10 Hz), 6.69-6.82(2H,m), 7.27-7.39(1H,m), 7.79(2H,s)

Workup

  1. additionTo the mixture was added, under ice-
  2. temperaturecooling
  3. extractionwas subjected to extraction with dichloromethane (30 ml)
  4. washThe extract was washed with water (20 ml)
  5. dry with materialdried (MgSO4)
  6. distillationThen the solvent was distilled off under reduced pressure
  7. customThe residue was purified by means of a silica gel chromatography (2.9×30 cm, eluent: ethyl acetate/methanol =25/1)
  8. concentrationThe object fraction was concentrated

Sources & evidence

ORD record
ord-1a4410eeef0f472b88f607c7f3a88fda
Source dataset
uspto-grants-1995_02
Patent number
US05389663

Reaction notes

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