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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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2-Methyl-6-nitrobenzoic anhydride → (3R,7S,10S,13R,14S)-7-benzyl-14-hydroxy-13-isopropyl-3-((E)-4-tritylsulfanyl-but-1-enyl)-10-tritylsulfanylmethyl-1,2-dioxa-4,9,12-triaza-cyclohexadecane-5,8,11,16-tetraone

HRID 888673
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HRID 888673 반응식
CC1C=CC=C([N+]([O-])=O)C=1C(OC(C1C([N+]([O-])=O)=CC=CC=1C)=O)=O.[OH:26][C@H:27]([C@H:32]([NH:36][C:37](=[O:101])[C@H:38]([NH:60][C:61](=[O:100])[C@H:62]([CH2:70][C:71](=[O:99])[NH:72][C@H:73]([OH:98])/[CH:74]=[CH:75]/[CH2:76][CH2:77][S:78][C:79]([C:92]1[CH:97]=[CH:96][CH:95]=[CH:94][CH:93]=1)([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)[CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[CH2:39][S:40][C:41]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH:33]([CH3:35])[CH3:34])[CH2:28][C:29]([OH:31])=[O:30]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:63]([C@@H:62]1[C:61](=[O:100])[NH:60][C@H:38]([CH2:39][S:40][C:41]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:37](=[O:101])[NH:36][C@H:32]([CH:33]([CH3:35])[CH3:34])[C@@H:27]([OH:26])[CH2:28][C:29](=[O:31])[O:30][O:98][C@H:73](/[CH:74]=[CH:75]/[CH2:76][CH2:77][S:78][C:79]([C:92]2[CH:93]=[CH:94][CH:95]=[CH:96][CH:97]=2)([C:86]2[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=2)[C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[NH:72][C:71](=[O:99])[CH2:70]1)[C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 86639715(3S,4R)-3-hydroxy-4-((S)-2-{(S)-2-[((E)-(R)-1-hydroxy-5-tritylsulfanyl-pent-2-enylcarbamoyl)-methyl]-3-phenyl-propionylamino}-3-tritylsulfanyl-propionylamino)-5-methyl-hexanoic acid

생성물 1

HCID 86639714(3R,7S,10S,13R,14S)-7-benzyl-14-hydroxy-13-isopropyl-3-((E)-4-tritylsulfanyl-but-1-enyl)-10-tritylsulfanylmethyl-1,2-dioxa-4,9,12-triaza-cyclohexadecane-5,8,11,16-tetraone수율 61.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of MNBA (54 mg, 0.16 mmol) and DMAP (38 mg, 0.31 mmol) in CH2Cl2 (29 mL) was added dropwise a solution of the acid 5A (137 mg, 0.13 mmol) in CH2Cl2 (117 mL) over 4.5 h, this was then stirred overnight at room temperature. The reaction mixture was washed sequentially with HCl (1M, 40 mL), sodium hydrogen carbonate (40 ml) and sat. brine (40 mL) before being dried (MgSO4), filtered and concentrated in vacuo to give a brown solid. Purification by column chromatography on silica gel (eluent 4:6-1:1 EtOAc/Hexane increased to 1:9 MeOH/CHCl3) gave 6A (79.4 mg, 0.08 mmol, 58%) as a white/brown solid: Rf 0.14 EtOAc/Hexane (4:6).

후처리

  1. washThe reaction mixture was washed sequentially with HCl (1M, 40 mL), sodium hydrogen carbonate (40 ml) and sat. brine (40 mL)
  2. dry with materialbefore being dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a brown solid
  6. customPurification by column chromatography on silica gel (eluent 4:6-1:1 EtOAc/Hexane increased to 1:9 MeOH/CHCl3)

출처 및 근거

ORD 기록
ord-68cc2c44f0784ad9babe48ce1c1c8577
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08247372B2

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