Dimethyl Sulfate → HCID 91043669, compound

HRID 897049Notes

Reaction equation

HRID 897049 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:34])[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][CH:31]=[CH:32][CH:33]=1)=[O:28])[C:23]([OH:25])=[O:24].[CH2:35]1CCN2C(=NCCC2)CC1.S(OC)(OC)(=O)=O>C(OCC)(=O)C>[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:34])[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][CH:31]=[CH:32][CH:33]=1)=[O:28])[C:23]([O:25][CH3:35])=[O:24]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86589029HCID 86589029, compound

Product 1

HCID 91043669HCID 91043669, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Step 1 (6.20 g) is dissolved in ethyl acetate (100 mL). DBU (2.20 g) and dimethyl sulphate (1.83 g) are added sequentially. The reaction mixture is stirred at room temperature for 2 hours, then partitioned between ethyl acetate and water. The organic layer is washed with water and brine, dried over magnesium sulphate and evaporated. Crystallisation from methanol affords furan-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 1H-NMR signals (CDCl3) δ 3.75 (3H, s), 6.30 (1H, dd), 6.45 (1H, d), 6.55 (2H, m), 7.15 (1H, d), 7.60 (1H, d).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customCrystallisation from methanol

Sources & evidence

ORD record
ord-014b69255deb4ffeb9ab13b37662ba7b
Source dataset
uspto-grants-2005_07
Patent number
US06921757B2

Reaction notes

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