Sodium Bicarbonate → 4-{3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methoxy-benzoylamino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 967458Notes

Reaction equation

HRID 967458 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:15]([OH:17])=O.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[C:45]([N:52]1[CH2:57][CH2:56][CH:55]([NH2:58])[CH2:54][CH2:53]1)([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:48]([O:47][C:45]([N:52]1[CH2:57][CH2:56][CH:55]([NH:58][C:15](=[O:17])[C:14]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:12]([O:11][CH2:10][CH2:9][C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[CH:13]=2)[CH2:54][CH2:53]1)=[O:46])([CH3:51])([CH3:49])[CH3:50]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 154803323-[2-(2,4-Dichlorophenyl)ethoxy]-4-methoxybenzoic acid

Product 1

HCID 696522964-{3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methoxy-benzoylamino}-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1 g 3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methoxy-benzoic acid in 15 ml CH2Cl2 1.5 ml N-NEM and subsequently 962 mg TOTU were added. After stirring for 1 h at RT 881 mg Boc-(4-amino)piperidine in 5 ml CH2Cl2 were added and the mixture was stirred for additional 2 h followed by addition of 20 ml saturated NaHCO3 solution. The organic layer was separated and dried over Na2SO4 and the solvent evaporated. The residue was recrystallized from ethyl acetate/heptane to afford a white powder.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customthe solvent evaporated
  5. customThe residue was recrystallized from ethyl acetate/heptane
  6. customto afford a white powder

Sources & evidence

ORD record
ord-35d0f54b09834de59ef94d31568ebf76
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

Loading…