Potassium Carbonate → HCID 86660782, compound

HRID 405017Notes

Reaction equation

HRID 405017 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([NH2:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[CH:8]=1)[CH3:2].[C:18]1([C:24](=NCC(OCC)=O)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.BrCC1C=CC(C#N)=C(F)C=1.C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC#N>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([N:16]=[C:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:4]([O:3][CH2:1][CH3:2])=[O:17])=[CH:8][C:9]=1[F:15])#[N:14]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 27784664-Cyano-3-fluorobenzyl bromideHCID 66630098HCID 66630098, compound

Product 1

HCID 86660782HCID 86660782, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Amino-3-(4-cyano-3-fluoro-phenyl)-propionic acid ethyl ester. In a 1.0 L flask, a mixture of ethyl 2-(diphenylmethyleneamino)acetate (267 g, 1.0 mol) and the catalyst Bu4NBr (32 g, 0.1 mol) in CH3CN (1000 mL) was treated sequentially with 4-(bromomethyl)-2-fluorobenzonitrile (232 g) and K2CO3 (276 g, 2 mol). The mixture was then stirred for 24 hrs at room temperature. The mixture was filtered and concentrated to give ethyl 3-(4-cyano-3-fluorophenyl)-2-(diphenylmethyleneamino)propanoate (400 g, 100% yield) as a yellow oil. The crude was treated with 2M HCl (600 mL) in THF (400 mL) overnight, and then extracted with EtOAc (3×200 mL). The water phase was basified with a saturated Na2CO3 to pH 10 and extracted with EtOAc (3×200 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to yield the title compound (153 g, yield 65% for the last three steps). The crude was not further purified and used straightly in next step.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a94ba0a42a7a4289877054447b2bc78a
Source dataset
uspto-grants-2014_06
Patent number
US08748412B2

Reaction notes

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