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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
ノート
印刷プレビュー

反応式

HRID 1481291 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 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]carbamate収率 97.1%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-330d741a956241f489300129d1885e1b
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409908B2

反応ノート

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