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

HRID 361752노트

반응식

HRID 361752 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-173b1748aa564d3fa2765318a8d9b901
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866592

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