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Ethylmorpholine → methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-(cinnamoylamino)pentyl}carbamoyl]indol-1-yl}acetate

HRID 2928
ノート
印刷プレビュー

反応式

HRID 2928 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C@H:20]([NH:26][C:27]([C:29]1[N:30]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[O:19].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:70](O)(=[O:79])[CH:71]=[CH:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1.C(N1CCOCC1)C>C(OCC)(=O)C.O.CN(C)C=O>[CH3:11][O:10][C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C@H:20]([NH:26][C:27]([C:29]1[N:30]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:70](=[O:79])[CH:71]=[CH:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)=[O:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 7525EthylmorpholineHCID 87842-Propenoic acid, 3-phenyl-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86752317methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-aminopentyl}carbamoyl]indol-1-yl}acetate

生成物 1

HCID 86752319
methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-(cinnamoylamino)pentyl}carbamoyl]indol-1-yl}acetate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-5 °C

実験手順

0.87 g of methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-aminopentyl}carbamoyl]indol-1-yl}acetate, 0.645 g of BOP and 0.23 g of cinnamic acid are successively added to 30 ml of dimethylformamide. After cooling to -5° C., 0.26 g of N-ethylmorpholine is added under an inert atmosphere and the reaction mixture is maintained at 0° C. for 2 hours and is then left at room temperature for 18 hours. The reaction mixture is poured into a large volume of water and extraction is carried out with ethyl acetate. The organic extracts are dried over anhydrous sodium sulphate and evaporated to dryness. The residual oil is purified by flash chromatography on silica gel, eluent: CH2Cl2 /CH3OH 97/3 (v/v) in order to obtain methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-(cinnamoylamino)pentyl}carbamoyl]indol-1-yl}acetate in the form of an oil.

後処理

  1. temperaturethe reaction mixture is maintained at 0° C. for 2 hours
  2. dry with materialThe organic extracts are dried over anhydrous sodium sulphate
  3. customevaporated to dryness
  4. customThe residual oil is purified by flash chromatography on silica gel, eluent

出典と根拠

ORDレコード
ord-92a29c6b2fb348a4acb80711b9b5d5dc
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05731340

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート