Hydrochloric Acid → HCID 59458880, compound

HRID 238868Notes

Reaction equation

HRID 238868 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]([C:22]2[CH:27]=[C:26]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[CH:25]=[C:24]([F:35])[CH:23]=2)([N+:20]#[C-])[CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[O:36][CH:37]([CH3:39])[CH3:38].Cl>CO.O1CCOCC1>[NH2:20][C@:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:36][CH:37]([CH3:39])[CH3:38])[CH:4]=1)([C:22]1[CH:27]=[C:26]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[CH:25]=[C:24]([F:35])[CH:23]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59458667HCID 59458667, compound

Product 1

HCID 59458880HCID 59458880, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-methyl 4-(2-(4-fluoro-3-isopropoxyphenyl)-2-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-isocyanoethyl)benzoate (120 mg, 0.22 mmol) in MeOH (2 mL) was added 4 N HCl in dioxane (0.5 mL) and the reaction mixture was stirred for 3 minutes. The reaction solvent was evaporated under a stream of nitrogen. The residue was diluted with EtOAc (15 mL), washed with saturated sodium bicarbonate solution (10 mL) and sat. NaCl, dried over MgSO4, filtered and evaporated to yield (R)-methyl 4-(2-amino-2-(4-fluoro-3-isopropoxyphenyl)-2-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)ethyl)benzoate (103 mg, 86% yield) as a clear glass. LCMS: RT=1.87 min [M−NH2] 525.1 (Phenomenex Luna C18 4.6×30 mm column, eluting with 10-90% MeOH/H2O containing 0.% TFA, 2 min gradient, flow rate 5 mL/min, wavelength 220 nm).

Workup

  1. customThe reaction solvent was evaporated under a stream of nitrogen
  2. additionThe residue was diluted with EtOAc (15 mL)
  3. washwashed with saturated sodium bicarbonate solution (10 mL) and sat. NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7b26e991e93942d39fa5fecca095c29d
Source dataset
uspto-grants-2014_02
Patent number
US08642576B2

Reaction notes

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