Dimethyl Sulfate → HCID 86589033, compound

HRID 897055Notes

Reaction equation

HRID 897055 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:38])[CH:9]([CH:10]4[CH2:11][C@H:12]([F:21])[C:13]5[C@@:18]([CH3:19])([C@:2]124)[CH:17]=[CH:16][C:15](=[O:20])[CH:14]=5)[CH2:8][C@@H:7]([CH3:22])[C@:6]3([O:26][C:27]([C:29]1[O:30][C:31]([O:34][C:35](=[O:37])[CH3:36])=[CH:32][CH:33]=1)=[O:28])[C:23]([OH:25])=[O:24].[CH2:39]1CCN2C(=NCCC2)CC1.S(OC)(OC)(=O)=O>C(OCC)(=O)C.Cl>[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:38])[CH:9]([CH:10]4[CH2:11][C@H:12]([F:21])[C:13]5[C@@:18]([CH3:19])([C@:2]124)[CH:17]=[CH:16][C:15](=[O:20])[CH:14]=5)[CH2:8][C@@H:7]([CH3:22])[C@:6]3([O:26][C:27]([C:29]1[O:30][C:31]([O:34][C:35](=[O:37])[CH3:36])=[CH:32][CH:33]=1)=[O:28])[C:23]([O:25][CH3:39])=[O:24]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86589034HCID 86589034, compound

Product 1

HCID 86589033HCID 86589033, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Step 1 (721 mg) is dissolved in ethyl acetate (25 mL). DBU (242 mg) is added, followed by dimethyl sulfate (201 mg) and the reaction is stirred at room temperature for 2 hours, then diluted with 0.2 M HCl. The organic phase is washed with water and brine, then dried over magnesium sulfate and evaporated. Purification by flash chromatography on silica gel eluting with hexanes-ethyl acetate (2:1) affords 5-acetoxyfuran-2-carboxylic acid (6S,9S,10S,11S,13S,16R,17R)-9,11-epoxy-6-fluoro-17-methoxycarbonyl-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester. Selected NMR signals (CDCl3) δ 0.96 (3H, d), 0.98 (3H, s), 1.40 (3H, s), 2.18 (3H, s), 2.76 (3H, s).

Workup

  1. washThe organic phase is washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customPurification by flash chromatography on silica gel eluting with hexanes-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-24fff0213a294e329c11733167be5dd4
Source dataset
uspto-grants-2005_07
Patent number
US06921757B2

Reaction notes

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