Hydrochloric Acid → HCID 89544869, compound

HRID 2283414Notes

Reaction equation

HRID 2283414 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([C:19](=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[CH:21]=2)[C:12]=1[F:29])[CH2:9][CH3:10])(C)(C)C.Cl.O1CCOCC1.[OH-].[Na+]>C(Cl)Cl.O>[NH2:7][C@@H:8]([C:11]1[C:12]([F:29])=[C:13]([C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:19]([C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[C:26]#[N:27])=[O:28])[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 89544838HCID 89544838, compound

Product 1

HCID 89544869HCID 89544869, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Step 5 {(R)-1-[3-(3-Cyano-benzoyl)-2-fluoro-4-methoxy-phenyl]-propyl}-carbamic acid tert-butyl ester (200 mg) was dissolved in DCM (5 mL), 4M HCl in dioxane (485 uL, 1.94 mmol, 4 eq) was added and the reaction mixture was stirred for 5 hours. Water was then added and the mixture was made basic with 1M NaOH. The organic phase was isolated by phase separator and combined and concentrated to give 3-[3-((R)-1-amino-propyl)-2-fluoro-6-methoxy-benzoyl]-benzonitrile.

Workup

  1. customThe organic phase was isolated by phase separator
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ec88ecec89484c11931ddbbf8dccd750
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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