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

HRID 2073322ノート

反応式

HRID 2073322 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2709567d454e4e4dabdfc0bfad3825a6
出典データセット
uspto-grants-1990_04
特許番号
US04916145

反応ノート

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