Chlorosuccinimide → HCID 178461660, compound

HRID 850090Notes

Reaction equation

HRID 850090 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:29])([C@H:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]=[N:26][NH:27][CH:28]=2)=[CH:20][CH:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[Cl:30]N1C(=O)CCC1=O>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:29])([C@H:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[NH:25][N:26]=[N:27][C:28]=2[Cl:30])=[CH:20][CH:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178461659HCID 178461659, compound

Product 1

HCID 178461660HCID 178461660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R,3S)-2-(2,4-difluorophenyl)-3-(4-[1,2,3-triazol-4-yl]phenyl)-1-(1,2,4-triazol-1-yl)butan-2-ol (2.0 g, 5 mmol-a product of Example 66) in dichloromethane (100 ml) was treated with N-chlorosuccinimide (0.81 g, 6 mmol). The mixture was stirred and irradiated at room temperature for 3 days then evaporated to dryness under reduced pressure. The residue was partitioned between ethyl acetate(50 ml) and saturated sodium bicarbonate (20 ml). The organic layer was washed with brine (20 ml), dried (Na2SO4) and evaporated to dryness under reduced pressure.

Workup

  1. customirradiated at room temperature for 3 days
  2. customthen evaporated to dryness under reduced pressure
  3. customThe residue was partitioned between ethyl acetate(50 ml) and saturated sodium bicarbonate (20 ml)
  4. washThe organic layer was washed with brine (20 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-55d7aaab06874dbca16a43ac1b9ca51e
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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