Triethylamine → (R)-3',4'-dimethoxy-2-(2-propenyl)-N-[1-methyl-4-(3-pyridinyl)butyl][1,1'-biphenyl]-4-carboxamide

HRID 2073322노트

반응식

HRID 2073322 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=O)=[CH:13][C:12]=2[CH2:20][CH:21]=[CH2:22])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:47][C@@H:48]([NH2:58])[CH2:49][CH2:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH:58][C@H:48]([CH3:47])[CH2:49][CH2:50][CH2:51][C:52]3[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=3)=[O:19])=[CH:13][C:12]=2[CH2:20][CH:21]=[CH2:22])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11062727(R)-2-Amino-5-(3-pyridyl)pentaneHCID 145701393',4'-Dimethoxy-2-(2-propenyl)[1,1'-biphenyl]-4-carboxylic acid

생성물 1

HCID 14570107(R)-3',4'-dimethoxy-2-(2-propenyl)-N-[1-methyl-4-(3-pyridinyl)butyl][1,1'-biphenyl]-4-carboxamide수율 93.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 379 mg of 3',4'-dimethoxy-2-(2-propenyl)[1,1'-biphenyl]-4-carboxylic acid in 8 mL of dimethylformamide was cooled in an ice bath and 0.19 mL of triethylamine and 0.30 mL of diphenylphosphorylazide were added. After 1 hour. 0.223 g of (R)-alpha-methyl-3-pyridinebutanamine was added and the reaction mixture was allowed to warm to room temperature over 48 hours. The mixture was diluted with ethyl acetate and washed with water and saturated potassium carbonate, dried. and concentrated. The residue was chromatographed over 50 g of silica gel, eluting with ethyl acetate to afford 527 mg of (R)-3',4'-dimethoxy-2-(2-propenyl)-N-[1-methyl-4-(3-pyridinyl)butyl][1,1'-biphenyl]-4-carboxamide as a water white oil.

후처리

  1. washwashed with water and saturated potassium carbonate
  2. customdried
  3. concentrationand concentrated
  4. customThe residue was chromatographed over 50 g of silica gel
  5. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-2709567d454e4e4dabdfc0bfad3825a6
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04916145

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