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

HRID 32053노트

반응식

HRID 32053 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
23.5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4c2016b6bd7c494fbbab0ec845cf3b29
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425631B2

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