Hydrochloric Acid → HCID 89408388, compound

HRID 516206Notes

Reaction equation

HRID 516206 reaction equation
[C:1]1([O:7][C:8](=[O:22])[NH:9][C@H:10]([C:14]2[C:19]([F:20])=[C:18]([Cl:21])[CH:17]=[CH:16][N:15]=2)[CH2:11][CH:12]=C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.ClC(OC1C=CC=CC=1)=[O:26]>CO.O1CCOCC1.C(#N)C.CCOC(C)=O>[C:1]1([O:7][C:8](=[O:22])[NH:9][C@H:10]([C:14]2[C:19]([F:20])=[C:18]([Cl:21])[CH:17]=[CH:16][N:15]=2)[CH2:11][CH:12]=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 15891Phenyl chloroformateHCID 131733334HCID 131733334, compound

Product 1

HCID 89408388HCID 89408388, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-Phenyl(1-(4-chloro-3-fluoropyridin-2-yl)but-3-en-1-yl)carbamate: To solution of Intermediate 15B (0.710 g, 1.329 mmol) in MeOH (10 mL) was added 4 M of HCl in dioxane (10 mL) and stirred at rt for 1 h. The reaction mixture was then concentrated and dried under vacuum. The crude product was then re-dissolved in TEA (1.623 mL, 11.65 mmol) and ACN (20 mL). To the above solution was then added phenyl chloroformate (0.321 mL, 2.56 mmol) dropwise and stirred at rt for 10 min. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was concentrated and the residue was purified by silica gel chromatography to yield the desired product (0.550 g, 74%). MS (ESI) m/z: 321.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customdried under vacuum
  3. washwashed with water
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fc59591a51274b289dd5d49986e82023
Source dataset
uspto-grants-2015_08
Patent number
US09108981B2

Reaction notes

Loading…