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Ethanol → (S)-3-[3-(5-Bromo-2-oxo-2,3-dihydro-benzothiazol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747488
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인쇄 미리보기

반응식

HRID 1747488 반응식
[CH2:1]([O:3][C:4](=[O:37])[CH2:5][C@@H:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[CH:25]=[C:24]([Br:26])[CH:23]=[C:22]([N+:27]([O-])=O)[C:21]=2[S:30][C:31](=[O:35])N(C)C)[C:11]1=[O:36])[CH2:7][CH2:8][CH3:9])[CH3:2].C(O)C.[Sn](Cl)(Cl)(Cl)Cl>C(OC(=O)C)C>[CH2:1]([O:3][C:4](=[O:37])[CH2:5][C@@H:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:21]3[S:30][C:31](=[O:35])[NH:27][C:22]=3[CH:23]=[C:24]([Br:26])[CH:25]=2)[C:11]1=[O:36])[CH2:7][CH2:8][CH3:9])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 702EthanolHCID 24287Tin tetrachlorideHCID 59497582(S)-3-[3-(5-Bromo-2-dimethylcarbamoylsulfanyl-3-nitro-benzyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

생성물 1

HCID 59497273(S)-3-[3-(5-Bromo-2-oxo-2,3-dihydro-benzothiazol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester수율 57.9%

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

반응 조건

온도
75 °C

실험 절차

(S)-3-[3-(5-Bromo -2-dimethylcarbamoylsulfanyl-3-nitro-benzyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (70 mg, 0.11 mmol) is suspended in ethylacetate (0.5 mL)/ethanol (0.5 mL) and then tin chloride (133 mg, 0.6 mmol) is added. The resulting suspension is equipped with a reflux condenser and heated to 75° C. for 1 hour. Upon completion the reaction is cooled to room temperature and the solvents evaporated in vacuo. The resulting solid is taken up in ethyl acetate and the product is filtered. The solvent is evaporated in vacuo and the resulting solid is purified via prep reverse phase LC to give 33 mg (54%) of the title compound. LCMS (ESMS): m/z 519.7 (M+H+).

후처리

  1. customThe resulting suspension is equipped with a reflux condenser
  2. temperatureUpon completion the reaction is cooled to room temperature
  3. customthe solvents evaporated in vacuo
  4. filtrationthe product is filtered
  5. customThe solvent is evaporated in vacuo
  6. customthe resulting solid is purified via prep reverse phase LC

출처 및 근거

ORD 기록
ord-5069da7b0bf048b58aeeccfefc152c8a
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150556B2

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