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

HRID 875173Notes

Reaction equation

HRID 875173 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 (75 g, 0.2757 moles) was added to a mixture of potassium carbonate (95.12 g), DM water (225 ml), ethyl acetate (450 ml) and L-valine methyl ester hydrochloride (55.45 g, 0.330 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., added DM water (375 ml) and adjusted the pH to 0.8-1.0 with dilute hydrochloric acid at 20-30° C. The aqueous layer was separated and extracted the product in to toluene (430 ml) by adjusting the pH to 8.0-8.5 with 20% w/w aqueous sodium carbonate solution. The toluene layer was washed with DM water (225 ml), concentrated under reduced pressure and dissolved in toluene (450 ml)

Workup

  1. customAfter completion of the reaction
  2. customthe ethyl acetate layer was separated at 20-30° C.
  3. additionadded DM water (375 ml)
  4. customat 20-30° C
  5. customThe aqueous layer was separated
  6. extractionextracted the product in to toluene (430 ml)
  7. washThe toluene layer was washed with DM water (225 ml)
  8. concentrationconcentrated under reduced pressure
  9. dissolutiondissolved in toluene (450 ml)

Sources & evidence

ORD record
ord-f80b27b44c134ce4b608391932b4f6e2
Source dataset
uspto-grants-2015_03
Patent number
US08981109B2

Reaction notes

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