Pyridine → tert-Butyl 3-(3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-2-methyl-phenyl)propanoate

HRID 1476134Notes

Reaction equation

HRID 1476134 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:18][C:19]1[C:20]([CH3:34])=[C:21]([CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:22]=[CH:23][CH:24]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.N1C=CC=CC=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:9]([NH:18][C:19]2[C:20]([CH3:34])=[C:21]([CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH:22]=[CH:23][CH:24]=2)=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58136633Tert-butyl 3-(3-amino-2-methylphenyl)propanoateHCID 58288396(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid

Product 1

HCID 58288217tert-Butyl 3-(3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-2-methyl-phenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 100 mg (0.38 mmol) of (2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid, 88 mg (0.38 mmol) of tert-butyl 3-(3-amino-2-methylphenyl)propanoate, 213 mg (0.56 mmol) of 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) and 1 ml of pyridine in 4 ml of DMF was stirred at room temperature overnight. After the reaction had ended, the reaction mixture was directly, without further work-up, separated into its components by preparative HPLC (mobile phase acetonitrile/water). This gave 151 mg (83% of theory) of the title compound as a colourless oil.

Workup

  1. customseparated into its components by preparative HPLC (mobile phase acetonitrile/water)

Sources & evidence

ORD record
ord-dffe20c1a85645e89d05a4cc9ea74555
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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