Triphosgene → HCID 57410216, compound

HRID 527688Notes

Reaction equation

HRID 527688 reaction equation
[NH2:1][C@H:2]([CH2:25][CH3:26])[C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[C:18]3[C:19]([CH:22]([CH3:24])[CH3:23])=[N:20][O:21][C:17]=3[CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:11]=1)=[O:4].Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH2:25]([C@H:2]1[NH:1][C:28](=[O:30])[N:5]([C:6]2[CH:7]=[N:8][C:9]([O:12][C:13]3[C:18]4[C:19]([CH:22]([CH3:23])[CH3:24])=[N:20][O:21][C:17]=4[CH:16]=[CH:15][CH:14]=3)=[CH:10][CH:11]=2)[C:3]1=[O:4])[CH3:26]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 67966862HCID 67966862, compound2×

Product 1

HCID 57410216HCID 57410216, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2R)-2-amino-N-(6-{[3-(1-methylethyl)-1,2-benzisoxazol-4-yl]oxy}-3-pyridinyl)butanamide (Intermediate 44) was dissolved in dichloromethane (1.0 ml) and TEA (3 μL, 0.022 mmol) was added. The reaction mixture was cooled down to 0° C. and triphosgene (0.6 mg, 1.98 μmol) was added and the mixture was stirred at that temperature for 30 minutes. The reaction mixture was quenched with water and water was removed by addition of sodium sulphate. The organic phase was pipetted off and evaporated and the residue obtained was charged on a silica gel column (Biotage SP1 system) and eluted with Cyhexane/EtOAc (from all 1/0 to 7/3, then 7/3, then from 7/3 to 1/1, then 1/1, then 0/1) to afford the title compound (1 mg).

Workup

  1. customThe reaction mixture was quenched with water and water
  2. customwas removed by addition of sodium sulphate
  3. customevaporated
  4. customthe residue obtained
  5. additionwas charged on a silica gel column (Biotage SP1 system)
  6. washeluted with Cyhexane/EtOAc (from all 1/0 to 7/3

Sources & evidence

ORD record
ord-407794a4c1144052bc6fabc4e4b6636f
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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