Triethylamine → benzyl (3R)-3-(4-cyanobenzoylamino)-4-(3-cyanophenoxy)butanoate

HRID 747705노트

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HRID 747705 반응식
C(O[C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])(C)(C)C.[C:31]([C:33]1[CH:41]=[CH:40][C:36](C(Cl)=O)=[CH:35][CH:34]=1)#[N:32].C(N(CC)CC)C.C(OCC)(=O)C>Cl.O1CCOCC1>[C:31]([C:33]1[CH:41]=[CH:40][C:36]([C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)[CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])=[O:7])=[CH:35][CH:34]=1)#[N:32]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 801724-Cyanobenzoyl chlorideHCID 10960575benzyl (3R)-3-t-butoxycarbonylamino-4-(3-cyanophenoxy)butyrate

생성물 1

HCID 11761964benzyl (3R)-3-(4-cyanobenzoylamino)-4-(3-cyanophenoxy)butanoate

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

1.8 g (4.38 mmol) of benzyl (3R)-3-t-butoxycarbonylamino-4-(3-cyanophenoxy)butyrate was dissolved in 20 ml of 4 N solution of hydrogen chloride in dioxane, and the solution was stirred at 0° C. for 6 hours. The solvent was evaporated, and the oily residue was dissolved in 5 ml of dichloromethane. 1.09 g (6.58 mmol) of 4-cyanobenzoyl chloride and 1.22 ml (8.76 mmol) of triethylamine were added to the solution under cooling with ice, and they were stirred at room temperature overnight. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe oily residue was dissolved in 5 ml of dichloromethane
  3. temperatureunder cooling with ice, and they
  4. stirringwere stirred at room temperature overnight
  5. customwhich was purified by the silica gel column chromatography

출처 및 근거

ORD 기록
ord-d7ecd08be8d841e3ae21f99f7fd3381e
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396844B1

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