Pyridine → HCID 86740235, compound

HRID 484931Notes

Reaction equation

HRID 484931 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.FC(F)(F)[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.[C:27]([CH2:29][C:30]([OH:32])=O)#N.[C:33]([O-:36])(=[O:35])C.[NH4+:37].C([C:40](=[CH:44][C:45]1[CH:50]=[CH:49][C:48](C(F)(F)F)=[CH:47][CH:46]=1)[C:41]([OH:43])=O)#N.FC(F)(F)[C:57]1[CH:62]=[CH:61][C:60]([CH:63]=CC#N)=[CH:59][CH:58]=1.[N:69]1[CH:74]=CC=CC=1>N.[Ni].C1(C)C=CC=CC=1>[CH2:63]([O:36][C:33]([NH:37][C@H:40]([C:41]([N:69]([CH3:74])[C@@H:29]([C:30]([NH:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:13])([F:14])[F:1])=[CH:8][CH:7]=1)=[O:32])[CH3:27])=[O:43])[CH2:44][C:45]1[CH:46]=[CH:47][C:48]([O:22][CH2:21][C:20]2[CH:19]=[CH:18][CH:17]=[CH:24][CH:23]=2)=[CH:49][CH:50]=1)=[O:35])[C:60]1[CH:59]=[CH:58][CH:57]=[CH:62][CH:61]=1

Participants

11

Reactant 7

HCID 1049PyridineHCID 9740Cyanoacetic acidHCID 679964-(Trifluoromethyl)benzaldehydeHCID 517165Ammonium AcetateHCID 147725463-[4-(Trifluoromethyl)phenyl]propan-1-amineHCID 54005872HCID 54005872, compoundHCID 57364308HCID 57364308, compound

Product 1

HCID 86740235HCID 86740235, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 1140TolueneSolvent

Procedure

By the method of part E of Example 1 (N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-N2 -methyl-D-alanyl hydrazide (3.0 g.) was condensed with 3-(4-trifluoromethylphenyl)propylamine (prepared by first condensing 4-trifluoromethylbenzaldehyde with cyanoacetic acid in refluxing toluene using a catalytic amount of ammonium acetate, then decarboxylating the resulting α-cyano-β-(4-trifluoromethylpheny)acrylic acid in refluxing pyridine, and finally hydrogenating the resulting β-(4-trifluoromethylphenyl)acrylonitrile in methanolic ammonia at room temperature and 400 p.s.i.g. pressure using Raney nickel catalyst, m.r. of hydrochloride salt 189°-191°; 1.42 g.). The product was crystallized from ethanol, affording (N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-N2 -methyl-N-[3-(4-trifluoromethylphenyl)propyl]-D-alaninamide (2.85 g., m.r. 120°-122° C.).

Workup

  1. customat room temperature
  2. customThe product was crystallized from ethanol

Sources & evidence

ORD record
ord-d120eb763a4d4bfeadc77f9cd8bd00e9
Source dataset
uspto-grants-1985_08
Patent number
US04533655

Reaction notes

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