Diisopropylethylamine → HCID 54050275, compound

HRID 1609195Notes

Reaction equation

HRID 1609195 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:12]([O:19][C:20](=[O:29])[CH2:21][NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[C:44]#[N:45])=[CH:34][CH:33]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:12]([O:19][C:20](=[O:29])[CH2:21][N:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[C:44]#[N:45])=[CH:36][CH:37]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 21693962HCID 21693962, compound

Product 1

HCID 54050275HCID 54050275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.8 g (60 mmol) of rac. phenylglycine benzyl ester tosylate and 8.2 g (30 mmol) of 4-bromomethyl-2'-cyanobiphenyl are kept at 80° with stirring for 2 hours together with 15.5 g of diisopropylethylamine (Hunig base) in 60 ml of DMF. The reaction mixture is then poured into ice-water and extracted with ethyl acetate. The ethyl acetate is separated off and stirred with 2N hydrochloric acid. The hydrochloride of the title compound which precipitates as an oil is separated off, converted into the base using sodium carbonate solution and further used in crude form (Rf 0.65 in system B7).

Workup

  1. customare kept at 80°
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate is separated off
  4. customThe hydrochloride of the title compound which precipitates as an oil
  5. customis separated off

Sources & evidence

ORD record
ord-d25f8e314f92433a9bbb205a5b0aedab
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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