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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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Sodium Azide → 17-(2-((5-Azidopentyl)oxy)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

HRID 2039395
ノート
印刷プレビュー

反応式

HRID 2039395 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]([CH:11]1[C:27]2([CH3:28])[CH:14]([CH:15]3[CH:24]([CH2:25][CH2:26]2)[C:23]2([CH3:29])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)=[O:10].[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C)C=O>[N:31]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]([CH:11]1[C:27]2([CH3:28])[CH:14]([CH:15]3[CH:24]([CH2:25][CH2:26]2)[C:23]2([CH3:29])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)=[O:10])=[N+:32]=[N-:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 8667556417-(2-((5-Bromopentyl)oxy)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

生成物 1

HCID 7118308317-(2-((5-Azidopentyl)oxy)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

To a solution of 7 (125 mg, 0.261 mmol) in anhydrous N,N-dimethylformamide (7 mL) was added sodium azide (169 mg, 2.61 mmol). The reaction mixture was heated to 65° C. and stirred overnight. Excess sodium azide was filtered off and the solvent was removed by rotary evaporation. The crude residue was dissolved in ethyl acetate and washed with water three times. The organic layer was dried over sodium sulfate and concentrated followed by flash chromatography in hexanes/ethyl acetate (2:1) to give 9 (78 mg, 68%). 1H NMR (500 MHz, CD3OD) δ 5.61 (d, J=4.9 Hz, 1H), 3.39 (t, J=6.4 Hz, 2H), 3.25-3.17 (m, 4H), 2.60 (t, J=9.1 Hz, 1H), 2.45-2.33 (m, 2H), 2.25-2.15 (m, 2H), 2.12-2.03 (m, 1H), 1.99 (m, 1H), 1.89-1.76 (m, 2H), 1.70-1.29 (m, 15H), 1.29-1.15 (m, 2H), 1.13 (d, J=11.0 Hz, 4H), 1.04-0.87 (m, 2H), 0.60 (s, 3H). 13C NMR (125 MHz, CD3OD) δ 210.81, 202.29, 174.92, 124.24, 78.00, 72.34, 62.71, 59.71, 57.39, 55.16, 52.43, 45.67, 39.99, 39.72, 36.81, 34.72, 33.90, 33.20, 30.15, 29.75, 25.52, 24.46, 24.17, 23.76, 22.15, 17.67, 13.96. ESI-MS m/z [M+Na]+ observed: 464.2, calculated: 464.3.

後処理

  1. filtrationExcess sodium azide was filtered off
  2. customthe solvent was removed by rotary evaporation
  3. dissolutionThe crude residue was dissolved in ethyl acetate
  4. washwashed with water three times
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d2b7005f53774e9db978ec53c7fc41cb
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08580231B2

反応ノート

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