Cesium carbonate → HCID 66701256, compound

HRID 2062101Notes

Reaction equation

HRID 2062101 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]([CH3:27])([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1OS(C(F)(F)F)(=O)=O)=[O:8])[CH3:5].[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:28])[C:4]([CH3:27])([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[NH:36][CH2:35][C:34]1[CH:33]=[CH:32][C:31]([C:30]([F:29])([F:39])[F:40])=[CH:38][CH:37]=1)=[O:8])[CH3:5]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 768044-(Trifluoromethyl)benzylamineHCID 634876Binap, (A+-)-HCID 86619675HCID 86619675, compound

Product 1

HCID 66701256HCID 66701256, compoundYield 94.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-2-[(1-trifluoromethanesulfonyloxy-naphthalene-2-carbonyl)-amino]-propionic acid methyl ester (142 mg), 4-trifluoromethyl benzyl amine (119 mg) and a catalytic amount of palladium acetate and BINAP, together with cesium carbonate (277 mg) in THF (3 ml) were heated in a microwave reactor for 55 min at 80° C. The reaction mixture was diluted with ethyl acetate (60 ml), which was washed with water (25 ml) and brine (10 ml) and then dried over sodium sulfate. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography. 142 mg of 2-methyl-2-{[1-(4-trifluoromethyl-benzylamino)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester was obtained as light yellow oil.

Workup

  1. washwas washed with water (25 ml) and brine (10 ml)
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4a2c076671e7480a86ccf3e4495b5967
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

Loading…