Sodium Hydroxide → HCID 136397841, compound

HRID 897056Notes

Reaction equation

HRID 897056 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:39])[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:27][C:28]([C:30]1[O:31][C:32]([O:35]C(=O)C)=[CH:33][CH:34]=1)=[O:29])[C:23]([O:25][CH3:26])=[O:24].[OH-].[Na+]>CO>[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:39])[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:27][C:28]([C:30]1[O:31][C:32]([OH:35])=[CH:33][CH:34]=1)=[O:29])[C:23]([O:25][CH3:26])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86589033HCID 86589033, compound

Product 1

HCID 136397841HCID 136397841, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Step 2 (555 mg) is dissolved in methanol (10 mL) and 2M methanolic sodium hydroxide (1 mL) is added. After 1 hour the solvent is evaporated and the residue partitioned between water and ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated. Purification by flash chromatography eluting with hexanes-ethyl acetate (1:1) affords 5-hydroxyfuran-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. TLC Rf 0.25 (1:1 hexane-ethyl acetate elution).

Workup

  1. customAfter 1 hour the solvent is evaporated
  2. customthe residue partitioned between water and ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated
  5. customPurification by flash chromatography
  6. washeluting with hexanes-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-d57e7e146081435f9b3269f610e3c5df
Source dataset
uspto-grants-2005_07
Patent number
US06921757B2

Reaction notes

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