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4-Nitrobenzenesulfonyl chloride → N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

HRID 714131
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HRID 714131 반응식
[NH2:1][C@H:2]([CH2:33][O:34][Si:35]([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:32])[C@H:13]([CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:14][C:15]([O:17][CH3:18])=[O:16].[N+:52]([C:55]1[CH:60]=[CH:59][C:58]([S:61](Cl)(=[O:63])=[O:62])=[CH:57][CH:56]=1)([O-:54])=[O:53].S(Cl)(Cl)(=O)=O>N1C=CC=CC=1>[Si:35]([O:34][CH2:33][C@@H:2]([NH:1][S:61]([C:58]1[CH:57]=[CH:56][C:55]([N+:52]([O-:54])=[O:53])=[CH:60][CH:59]=1)(=[O:62])=[O:63])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:32])[C@H:13]([CH:19]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:14][C:15]([O:17][CH3:18])=[O:16])([C:48]([CH3:51])([CH3:50])[CH3:49])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 24648Sulfuryl chlorideHCID 68029330N-{2-[(3S)-3-amino-4-{[tert-butyl(diphenyl)silyl]oxy}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

생성물 1

HCID 86708031N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide수율 101.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of N-{2-[(3S)-3-amino-4-{[tert-butyl(diphenyl)silyl]oxy}butyl]phenyl}-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (8, 255.1 mg, 0.364 mmol) in pyridine (2 mL) was treated with solid p-nitro benzenesulfonyl chloride (247 mg, 1.115 mmol) (or any other suitable sulfonyl chloride) and the mixture stirred at room temperature for 13 h, quenched with sat. NaHCO3 (0.5 mL), diluted with DCM, washed with sat. NaHCO3 then aqueous 5% KHSO4 then saturated NaHCO3, dried over MgSO4, filtered and concentrated to get 326 mg (100% yield) of the title compound, which was used without further purification for the next step. MS: m/z=885.3 (MH+).

후처리

  1. customquenched with sat. NaHCO3 (0.5 mL)
  2. additiondiluted with DCM
  3. washwashed with sat. NaHCO3
  4. dry with materialaqueous 5% KHSO4 then saturated NaHCO3, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-183eece9483d48bb9170456eed671bd5
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187415B2

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