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Dexamethasone → 2-(2-(2-((8S,9R,10S,11S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[alpha]phenanthren-17-yl)-2-oxoethoxy)-2-oxoethylsulfinyl)ethyl methacrylate methacrylate

HRID 523622
ノート
印刷プレビュー

反応式

HRID 523622 の反応式
[C:1]([O:6][CH2:7][CH2:8][S:9]([CH2:11][C:12]([OH:14])=[O:13])=[O:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:15][C@H:16]1[C@:33]([OH:38])([C:34]([CH2:36]O)=[O:35])[C@:32]2([CH3:39])[C@H:18]([C@H:19]3[C@:29]([F:41])([C@@H:30]([OH:40])[CH2:31]2)[C@:28]2([CH3:42])[C:22](=[CH:23][C:24]([CH:26]=[CH:27]2)=[O:25])[CH2:21][CH2:20]3)[CH2:17]1.C1CCC(N=C=NC2CCCCC2)CC1.CCOC(C)=O>C1COCC1.CN(C1C=CN=CC=1)C>[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:1]([O:6][CH2:7][CH2:8][S:9]([CH2:11][C:12]([O:14][CH2:36][C:34]([C@:33]1([OH:38])[C:32]2([CH3:39])[CH:18]([C@H:19]3[C@:29]([F:41])([C@@H:30]([OH:40])[CH2:31]2)[C@:28]2([CH3:42])[C:22](=[CH:23][C:24](=[O:25])[CH:26]=[CH:27]2)[CH2:21][CH2:20]3)[CH2:17][C@H:16]1[CH3:15])=[O:35])=[O:13])=[O:10])(=[O:5])[C:2]([CH3:4])=[CH2:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5743DexamethasoneHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 871700522-(2-(Methacryloyloxy)ethylsulfinyl)acetic acid

生成物 1

HCID 1317355722-(2-(2-((8S,9R,10S,11S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[alpha]phenanthren-17-yl)-2-oxoethoxy)-2-oxoethylsulfinyl)ethyl methacrylate methacrylate
収率 73%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

5 (0.54 g, 2.4 mmol, 1.05 eqv.) was dissolved in dry THF (5 mL) and DMAP (0.14 g, 1.2 mmol, 0.5 eqv.) was added to the solution under nitrogen. After cooling on ice, a dexamethasone solution (0.91 g, 2.3 mmol, 1 eqv.) in dry THF (25 mL) and DCC (0.525 g, 2.5 mmol, 1.1 eqv.) were added to the mixture. The reaction mixture was slowly warmed to room temperature and stirred overnight at RT. The completion of the reaction was confirmed by TLC (EtOAc/Hex, 20:1 (v/v), Rf: 0.24). Most of the solvent was evaporated and the remaining solution was purified on a 20 cm silica gel column (EtOAc/Hex, 20:1 (v/v)). 1 g (73% yield) DMSL2 was obtained as a yellow fluffy solid.

後処理

  1. temperatureAfter cooling on ice
  2. customMost of the solvent was evaporated
  3. customthe remaining solution was purified on a 20 cm silica gel column (EtOAc/Hex, 20:1 (v/v))
  4. customwas obtained as a yellow fluffy solid

出典と根拠

ORDレコード
ord-2104005dace845429e12138a9e8602c3
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09339554B2

反応ノート

読み込み中…

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