Triethylamine → 2-Ethynyl-3'',4''-dimethoxy-biphenyl-4-carboxylic acid (1-methyl-4-pyridin-3-yl-butyl)-amide

HRID 2073300ノート

反応式

HRID 2073300 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](O)=[O:18])=[CH:13][C:12]=2[C:20]#[CH:21])[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.[CH3:46][C@@H:47]([NH2:57])[CH2:48][CH2:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1>CN(C)C=O.C(OCC)(=O)C>[C:20]([C:12]1[CH:13]=[C:14]([C:17]([NH:57][C@H:47]([CH3:46])[CH2:48][CH2:49][CH2:50][C:51]2[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=2)=[O:18])[CH:15]=[CH:16][C:11]=1[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)#[CH:21]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11062727(R)-2-Amino-5-(3-pyridyl)pentaneHCID 145701343',4'-Dimethoxy-2-ethynyl[1,1'-biphenyl]-4-carboxylic acid

生成物 1

HCID 145701032-Ethynyl-3'',4''-dimethoxy-biphenyl-4-carboxylic acid (1-methyl-4-pyridin-3-yl-butyl)-amide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 459 mg of 3',4'-dimethoxy-2-ethynyl[1,1'-biphenyl]-4-carboxylic acid in 8 mL of dimethylformamide was cooled in an ice bath and treated with 0.25 mL of triethylamine and 0.38 mL of diphenylphosphoryl azide. After 1 hour. 0.3 mL of (R)alpha-methyl-3-pyridinebutanamine was added and the reaction mixture was allowed to warm to room temperature over 48 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried and concentrated. The residue was chromatographed over 50 g of silica gel eluting with ethyl acetate and the product was crystallized from ethyl acetate-hexane to give 576 mg of (R)-2-Ethynyl-3',4'-dimethoxy-N-[1-methyl-4-(3-pyridinyl)butyl][1.1'-biphenyl]-4-carboxamide, mp 135°-137° C.

後処理

  1. washwashed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was chromatographed over 50 g of silica gel eluting with ethyl acetate
  5. customthe product was crystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-ce066783a42247559d200bdd11fbcd1e
出典データセット
uspto-grants-1990_04
特許番号
US04916145

反応ノート

読み込み中…