Dinoprost → Prostaglandin E2

HRID 2186531Notes

Reaction equation

HRID 2186531 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24]>CS(C)=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:12](=[O:23])[CH2:11][C@H:10]1[OH:24]

Participants

3

Reactant 1

HCID 5280363Dinoprost

Product 1

HCID 5280360Prostaglandin E2

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The scheme (A) indicates that a regioselectively silylated compound, i.e., bis-triethylsilyl-PGF2α, triethylsilyl ester, can be obtained by reacting PGF2α, with TESiD under 15˜35° C. for 18˜36 hours. Next, the oxidation of the 9-hydroxy group into ketone group is carried out by reacting with a Cr (VI)-based reagent under 15˜35° C. for 10˜15 minutes or activated dimethyl sulfoxide reagent under −78° C. for 2˜3 hours. Last, PGE2 is obtained via a desilylation reaction performed in an acidic aqueous solution reagent having pH=4˜6 under 15˜35° C. for 12˜24 hours.

Workup

  1. customcan be obtained
  2. waitwith TESiD under 15˜35° C. for 18˜36 hours
  3. customunder 15˜35° C.
  4. customfor 10˜15 minutes

Sources & evidence

ORD record
ord-f61adb9b8ab148fb99124e4111fb4dfd
Source dataset
uspto-grants-2002_06
Patent number
US06403817B1

Reaction notes

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