Trifluoroacetic acid → HCID 9861312, compound

HRID 890621Notes

Reaction equation

HRID 890621 reaction equation
C(OC([NH:8][C:9]1[C:19]([CH3:20])=[CH:18][C:12]([O:13][CH2:14][C:15]([OH:17])=O)=[C:11]([CH3:21])[C:10]=1[CH3:22])=O)(C)(C)C.C(OC([N:30]1[CH2:35][CH2:34][CH:33]([NH:36][CH3:37])[CH2:32][CH2:31]1)=O)(C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+].FC(F)(F)C(O)=O>CN(C)C=O.C(Cl)Cl.C(N(CC)CC)C>[NH2:8][C:9]1[C:19]([CH3:20])=[CH:18][C:12]([O:13][CH2:14][C:15]([N:36]([CH3:37])[CH:33]2[CH2:34][CH2:35][NH:30][CH2:31][CH2:32]2)=[O:17])=[C:11]([CH3:21])[C:10]=1[CH3:22]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylateHCID 22048569HCID 22048569, compound

Product 1

HCID 9861312HCID 9861312, compoundYield 82.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 1.86 g of 2-[4-(tert-butoxycarbonylamino)-2,3,5-trimethylphenoxy]acetic acid, 1.43 g of 1-(tert-butoxycarbonyl)-4-methylaminopiperidine, 2.94 g of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP Reagent) and 1.26 ml of triethylamine in 30 ml of dimethylformamide was stirred over night at room temperature. Then, 15 ml of saturated sodium hydrogen carbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried and concentrated under reduced pressure to give a residue. The obtained residue was dissolved in 30 ml of methylene chloride, and to this solution was added 7.5 ml of trifluoroacetic acid at 0° C., then the mixture was stirred for 2 hours at room temperature. After removal of the solvent, the resultant residue was purified by silica gel column chromatography (methylene chloride:methanol=12:1) to give 1.52 g (81%) of the above-mentioned compound (1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue
  6. customAfter removal of the solvent
  7. customthe resultant residue was purified by silica gel column chromatography (methylene chloride:methanol=12:1)

Sources & evidence

ORD record
ord-b26d7504d77d4a158e4514fdc554f6d6
Source dataset
uspto-grants-2006_02
Patent number
US06998401B2

Reaction notes

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