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Tetrabutylammonium Fluoride → 6-[Cyclopropyl-(3-methoxy-2-methylbenzyl)carbamoyl]-7-[5-(2-hydroxyethyl)-4-methylthiazol-2-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

HRID 1096847
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HRID 1096847 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:10]([CH2:11][C:12]([C:40]3[S:41][C:42]([CH2:46][CH2:47][O:48][Si](C(C)(C)C)(C)C)=[C:43]([CH3:45])[N:44]=3)=[C:13]2[C:24](=[O:39])[N:25]([CH:36]2[CH2:38][CH2:37]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[C:28]=2[CH3:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH:10]([CH2:11][C:12]([C:40]3[S:41][C:42]([CH2:46][CH2:47][OH:48])=[C:43]([CH3:45])[N:44]=3)=[C:13]2[C:24](=[O:39])[N:25]([CH:36]2[CH2:38][CH2:37]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[C:28]=2[CH3:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 685718207-{5-[2-(tert-Butyldimethylsilanyloxy)ethyl]-4-methylthiazol-2-yl}-6-[cyclopropyl-(3-methoxy-2-methylbenzyl)carbamoyl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

생성물 1

HCID 690859126-[Cyclopropyl-(3-methoxy-2-methylbenzyl)carbamoyl]-7-[5-(2-hydroxyethyl)-4-methylthiazol-2-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester수율 85.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A sol. of compound E1 (7.93 g, 9.45 mmol) and TBAF (1.0 M in THF, 14.5 mL, 14.5 mmol) in THF (115 mL) was stirred at 0° C. for 1 h. The mixture was diluted with EtOAc (115 mL) and was then washed with brine (4×115 mL). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:2→1:1→3:2→7:3) yielded the title compound (5.54 g, 76%). LC-MS: tR=1.08 min, ES+: 683.27.

후처리

  1. washwas then washed with brine (4×115 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (EtOAc/heptane 1:2→1:1→3:2→7:3)

출처 및 근거

ORD 기록
ord-11b601ae59614a9e9b7c500c186d4d56
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138340B2

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