Water → HCID 86589032, compound

HRID 897053Notes

Reaction equation

HRID 897053 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:36])[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[CH:34]=[N:33][C:32]([CH3:35])=[CH:31][N:30]=1)=[O:28])[C:23]([OH:25])=[O:24].[CH2:37]1CCN2C(=NCCC2)CC1.S(OC)(OC)(=O)=O.O>CN(C=O)C>[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:36])[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[CH:34]=[N:33][C:32]([CH3:35])=[CH:31][N:30]=1)=[O:28])[C:23]([O:25][CH3:37])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86589031HCID 86589031, compound

Product 1

HCID 86589032HCID 86589032, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The product of Step 1 (2.50 g) is dissolved in DMF (11 mL) and cooled to 0° C. DBU (1.68 g) is added, followed by dimethyl sulphate (953 mg) after 10 minutes. The reaction is stirred at room temperature for 2 hours, poured into water and extracted with ethyl acetate. The combined organic phases are washed with water and brine, then dried over sodium sulfate. Evaporation affords 5-methylpyrazine-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. Observed mass (M+H) 511.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customEvaporation

Sources & evidence

ORD record
ord-21bb32829d0f4bc6bbc2823fd783f36e
Source dataset
uspto-grants-2005_07
Patent number
US06921757B2

Reaction notes

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