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

Reaction equation

HRID 523622 reaction equation
[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]

Participants

7

Reactant 4

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

Product 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 methacrylateYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2104005dace845429e12138a9e8602c3
Source dataset
uspto-grants-2016_05
Patent number
US09339554B2

Linked notes

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