1,2-Dichloroethane → N-(7-cyano-chroman-4-yl)-3-(naphthalen-2-ylsulfonylamino)-3-phenyl-propionamide

HRID 32053ノート

反応式

HRID 32053 の反応式
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[S:24]([NH:27][CH:28]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:29][C:30](O)=[O:31])(=[O:26])=[O:25].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>C(Cl)Cl>[C:12]([C:8]1[CH:7]=[C:6]2[C:11]([CH:2]([NH:1][C:30](=[O:31])[CH2:29][CH:28]([NH:27][S:24]([C:15]3[CH:16]=[CH:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)(=[O:26])=[O:25])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:3][CH2:4][O:5]2)=[CH:10][CH:9]=1)#[N:13]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 36326413-(naphthalene-2-sulfonamido)-3-phenylpropionic AcidHCID 223499724-Aminochroman-7-carbonitrile

生成物 1

HCID 68934380N-(7-cyano-chroman-4-yl)-3-(naphthalen-2-ylsulfonylamino)-3-phenyl-propionamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
23.5 °C

実験手順

4-Amino-chroman-7-carbonitrile (Step E) (50 mg, 0.28 mmol), 3-(naphthalen-2-ylsulfonylamino)-3-phenyl-propionic acid (100 mg, 0.28 mmol), HOBt (42 mg, 0.31 mmol), and DIEA (72 mg, 0.56 mmol) were dissolved in CH2Cl2 (10 mL). EDC (52 mg, 0.34 mmol) was added and the reaction was stirred at 22-25° C. overnight until completed. The reaction solution was washed with dilute (˜5%) NaHCO3—H2O and H2O, and solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified by column chromatography (silica gel, 25% hexane in EtOAc) to provide the title compound as a white solid mixture of diastereomers (ca. 3:2 by 1H NMR after flash column chromotography).

後処理

  1. washThe reaction solution was washed
  2. additionwith dilute (˜5%) NaHCO3—H2O and H2O, and solution
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue which
  7. customwas purified by column chromatography (silica gel, 25% hexane in EtOAc)
  8. customto provide

出典と根拠

ORDレコード
ord-4c2016b6bd7c494fbbab0ec845cf3b29
出典データセット
uspto-grants-2008_09
特許番号
US07425631B2

反応ノート

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