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tert-Butyl N-[(10R,11E,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,11,15,17-heptaen-14-yl]carbamate → tert-Butyl N-[(10R,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]carbamate

HRID 1481291
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HRID 1481291 반응식
[CH3:1][C@H:2]1[C:3](=[O:29])[NH:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:11]2[CH:12]=[CH:13][N:14]=[C:15]([CH:28]=2)[C@@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:17][CH:18]=[CH:19]1>CCOC(C)=O.[Pt](=O)=O>[CH3:1][C@@H:2]1[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[C:15]2[CH:28]=[C:11]([CH:12]=[CH:13][N:14]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][C:3]1=[O:29]
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참가 물질

4

반응물 1

HCID 126739861tert-Butyl N-[(10R,11E,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,11,15,17-heptaen-14-yl]carbamate

생성물 1

HCID 131736623tert-Butyl N-[(10R,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]carbamate수율 97.1%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 8857Ethyl Acetate용매

실험 절차

45F (974 mg, 2.475 mmol) in EtOAc (49.500 mL) was added platinum(IV) oxide (56.2 mg, 0.248 mmol). The reaction mixture was charged with H2 balloon and vacuum/H2 several times. The reaction was stirred at rt under H2 overnight. The reaction was filtered and concentrated to give the desired product (0.95 g, 97%) as a brownish solid. 1H NMR (500 MHz, CHLOROFORM-d) δ 8.68 (d, J=5.0 Hz, 1H), 7.47-7.30 (m, 5H), 7.26-7.22 (m, 1H), 6.79 (br. s., 1H), 5.85 (d, J=7.7 Hz, 1H), 4.74 (br. s., 1H), 2.52-2.42 (m, 1H), 2.18-2.07 (m, 1H), 1.66-1.57 (m, 1H), 1.51-1.46 (m, 1H), 1.43 (s, 9H), 1.40-1.33 (m, 1H), 1.07 (br. s., 1H), 1.00 (d, J=6.9 Hz, 3H), 0.83 (d, J=9.9 Hz, 1H). MS (ESI) m/z: 396.2 (M+H)+.

후처리

  1. additionThe reaction mixture was charged with H2 balloon and vacuum/H2 several times
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-330d741a956241f489300129d1885e1b
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409908B2

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