Water → HCID 131734648, compound

HRID 1771132Notes

Reaction equation

HRID 1771132 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:3]=1[CH2:4][CH:5]1[CH2:7][N@:6]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].O.[C-:25]#[N:26].[K+].ClCCl>CS(C)=O>[C:25]([CH2:7][C@H:5]([NH:6][C:8](=[O:9])[O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:4][C:3]1[CH:18]=[C:19]([F:23])[C:20]([F:22])=[CH:21][C:2]=1[F:1])#[N:26]

Participants

6

Reactant 4

HCID 962Water2×HCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 131734649HCID 131734649, compound

Product 1

HCID 131734648HCID 131734648, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

15.78 g of (R)-benzyl 2-(2,4,5-trifluorobenzyl)aziridine-1-carboxylate was dissolved in 63.2 mL of dimethylsulfoxide and 15.8 mL of water in 250 mL flask; then 7.89 g of silicagel was added thereto. 6.40 g of potassiumcyanide was slowly added to the reaction solution, and the resulting reaction solution was stirred for 24 hours at 50° C. The reaction solution was cooled to room temperature, and then 160 mL of dichloromethane and 800 mL of water were added to the cooled reaction solution in order. An organic layer was isolated; washed with 80 mL of water in twice; dehydrated with sodium sulfate; and then concentrated under reduced pressure. 80 mL of diisopropylether was added to the concentrated residue and then the resulting concentrated residue was stirred for 1 hour at room temperature. The resulting solid was decompression-filtered and vacuum-dried to obtain 14.66 g of a title compound.

Workup

  1. additionthen 7.89 g of silicagel was added
  2. customthe resulting reaction solution
  3. temperatureThe reaction solution was cooled to room temperature
  4. customAn organic layer was isolated
  5. washwashed with 80 mL of water in twice
  6. concentrationand then concentrated under reduced pressure
  7. addition80 mL of diisopropylether was added to the concentrated residue
  8. stirringthe resulting concentrated residue was stirred for 1 hour at room temperature
  9. filtrationThe resulting solid was decompression-filtered
  10. customvacuum-dried

Sources & evidence

ORD record
ord-8e080d4c795640b68a913096eb0c4ef1
Source dataset
uspto-grants-2016_02
Patent number
US09249109B2

Reaction notes

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