Diethyl Ether → (3S)-3-[(1-Methylindole-2-Carbonyl)Leucinyl]Amino4-Oxobutanoic Acid, t-Butyl Ester Semicarbazone

HRID 1417432ノート

反応式

HRID 1417432 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([OH:13])=O.[NH2:14][C@H:15]([C:20]([NH:22][C@H:23]([CH:36]=[O:37])[CH2:24][C:25](=[N:31][NH:32][C:33]([NH2:35])=[O:34])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18].CCN=C=NCCCN(C)C.CCOCC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:14][C@H:15]([C:20]([NH:22][C@H:23]([CH:36]=[O:37])[CH2:24][C:25](=[N:31][NH:32][C:33]([NH2:35])=[O:34])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:21])[CH2:16][CH:17]([CH3:18])[CH3:19])=[O:13]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 865839973(S)-(Leucinyl)amino-4-oxobutanoic acid, t-butyl ester semicarbazone

生成物 1

HCID 86583996(3S)-3-[(1-Methylindole-2-Carbonyl)Leucinyl]Amino4-Oxobutanoic Acid, t-Butyl Ester Semicarbazone収率 80%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

1-Methylindole-2-carboxylic acid (70 mg, 0.4 mmol) and 3(S)-(Leucinyl)amino-4-oxobutanoic acid, t-butyl ester semicarbazone (131 mg, 0.4 mmol) were dissolved in methylene chloride (2 mL) and both DMAP (49 mg, 0.40 mmol) and EDAC (107 mg, 0.56 mmol) were added to the solution under a nitrogen atmosphere at 0° C. Stirring was continued for 1 hour at 0° C. and an additional 3 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and 5% KHSO4 solution. The ethyl acetate solution was washed successively with 5% KHSO4 solution, saturated with sodium bicarbonate solution (2×) and brine, dried over sodium sulfate, and concentrated in vacuo to give a crude solid. Trituration of the solid with ether afforded the title product as a white powder (156 mg, 80%). TLC(methanol/methylene chloride, 5/95, silica gel): Rf =0.42; 1H-NMR (CDCl3 +CD3OD): δ 8.18 (s, 1H), 7.66-7.11 (m, 6H), 6.97 (s, 1H), 6.32 (d, J=7.7, 1H), 4.95-4.88 (m, 1H), 4.70-4.62 (m, 1H), 4.03 (s, 3H), 2.82-2.56 (m, 2H), 1.87-1.58 (m, 3H), 1.38 (9H), 1.00 (t, J=6.3, 6H).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and 5% KHSO4 solution
  2. washThe ethyl acetate solution was washed successively with 5% KHSO4 solution, saturated with sodium bicarbonate solution (2×) and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a crude solid

出典と根拠

ORDレコード
ord-666abf93533448bba49e6fd3d380ca55
出典データセット
uspto-grants-1999_03
特許番号
US05877197

反応ノート

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