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

반응식

HRID 523622 반응식
[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]

참가 물질

7

반응물 4

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

생성물 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 methacrylate수율 73%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2104005dace845429e12138a9e8602c3
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09339554B2

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