Triethylamine → N-4-cyanobenzoyl-beta-m-chlorophenyl-alpha,alpha-dimethyl-beta-alanyl-4-piperidineacetic acid methyl ester

HRID 361752Notes

Reaction equation

HRID 361752 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:11]([CH3:16])([CH3:15])[C:12](O)=[O:13])=[O:8])=[CH:5][CH:4]=1)#[N:2].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH3:60][O:61][C:62](=[O:70])[CH2:63][CH:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1>C(Cl)Cl>[CH3:60][O:61][C:62](=[O:70])[CH2:63][CH:64]1[CH2:65][CH2:66][N:67]([C:12](=[O:13])[C:11]([CH3:15])([CH3:16])[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:25][CH:24]=2)[CH2:68][CH2:69]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1515259Methyl 4-piperidineacetateHCID 10713311N-4-Cyanobenzoyl-beta-m-chlorophenyl-alpha,alpha-dimethyl-beta-alanine

Product 1

HCID 10791393N-4-cyanobenzoyl-beta-m-chlorophenyl-alpha,alpha-dimethyl-beta-alanyl-4-piperidineacetic acid methyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-4-Cyanobenzoyl-β-m-chlorophenyl-α,α-dimethyl-β-alanine (300 mg, 0.84 mmol) was dissolved in methylene chloride (30 ml). To the resulting solution, BOP reagent (409 mg, 0.92 mmol) and triethylamine (1 ml) were added under cooling with ice and the mixture was stirred for 30 minutes. To the reaction mixture was added 4-piperidineacetic acid methyl ester (572 mg, 3.36 mmol) and the resulting mixture was stirred overnight. After the solvent was distilled off, the residue was applied to a silica gel column (2.2×20 cm) and eluted with a mixed solution (hexane:ethyl acetate=3:1). The desired fractions were collected and the solvents were distilled off to yield an oil of N-4-cyanobenzoyl-β-m-chlorophenyl-α,α-dimethyl-β-alanyl-4-piperidineacetic acid methyl ester (270 mg, 65.0%).

Workup

  1. temperatureunder cooling with ice
  2. stirringthe resulting mixture was stirred overnight
  3. distillationAfter the solvent was distilled off
  4. washeluted with a mixed solution (hexane:ethyl acetate=3:1)
  5. customThe desired fractions were collected
  6. distillationthe solvents were distilled off

Sources & evidence

ORD record
ord-173b1748aa564d3fa2765318a8d9b901
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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