4-Chlorophenyl Isocyanate → HCID 131735647, compound

HRID 530637Notes

Reaction equation

HRID 530637 reaction equation
[F:1][C:2]([F:20])([F:19])[C@@H:3]([OH:18])[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:6]1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>C(#N)C.CS(C)=O>[ClH:21].[F:20][C:2]([F:1])([F:19])[C@@H:3]([O:18][C:29](=[O:30])[NH:28][C:25]1[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=1)[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:6]1

Participants

5

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 117870991HCID 117870991, compound

Product 1

HCID 131735647HCID 131735647, compoundYield 118.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 6342AcetonitrileSolvent

Procedure

(2 S)-1,1,1-trifluoro-3-(2-(4-fluorophenyl)morpholino)propan-2-ol (39 mg, 133 μmol), TEA (92.7 μL, 665 μmol) and 1-chloro-4-isocyanatobenzene (20.4 mg, 133 μmol) were combined in 2 mL of acetonitrile and stirred at room temperature overnight. Several drops of DMSO were added to the mixture to make a clear solution. The solution was separated by reverse phase column chromatography (50-100% acetonitrile in water). The desired fractions were pooled, treated with 5 drops of conc. HCl and the solution lyophilized to afford the title compound (38 mg, 59%) as a white solid. (M+H)+=447 m/e.

Workup

  1. customThe solution was separated by reverse phase column chromatography (50-100% acetonitrile in water)
  2. additiontreated with 5 drops of conc. HCl

Sources & evidence

ORD record
ord-836a1ef359f341bcb2033709b184366e
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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