Water → N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-L-valine methyl ester

HRID 875174Notes

Reaction equation

HRID 875174 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].O.Cl.[CH3:25][O:26][C:27](=[O:33])[C@H:28]([CH:30]([CH3:32])[CH3:31])[NH2:29]>C(OCC)(=O)C>[CH3:25][O:26][C:27](=[O:33])[C@H:28]([CH:30]([CH3:32])[CH3:31])[NH:29][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 111190Methyl valinate hydrochlorideHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 16744794N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-L-valine methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

4′-Bromomethyl-2-cyanobiphenyl (15 g, 0.0551 moles) was added to a mixture of potassium carbonate (19.05 g), DM water (45 ml), ethyl acetate (60 ml) and L-valine methyl ester hydrochloride (11.09 g, 0.066 moles) at 20-30° C. The reaction mixture was heated to 40-50° C. and stirred for 25 h. After completion of the reaction, the ethyl acetate layer was separated at 20-30° C., concentrated under reduced pressure and dissolved in o-xylene (90 ml)

Workup

  1. customAfter completion of the reaction
  2. customthe ethyl acetate layer was separated at 20-30° C.
  3. concentrationconcentrated under reduced pressure
  4. dissolutiondissolved in o-xylene (90 ml)

Sources & evidence

ORD record
ord-ff9feba331b74dfdb9cf9c1fc8999a9b
Source dataset
uspto-grants-2015_03
Patent number
US08981109B2

Reaction notes

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