(5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal)
(5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal)
CAS: 126690-41-3
Molecular Formula: C32H45NO6
(5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal) - Names and Identifiers
(5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal) - Physico-chemical Properties
| Molecular Formula | C32H45NO6 |
| Molar Mass | 539.71 |
| Density | 1.27 |
| Boling Point | 697.0±55.0 °C(Predicted) |
| pKa | 14.69±0.70(Predicted) |
(5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal) - Reference Information
| Application | (5A,11B)-11-[4-(dimethylamino) phenyl]-5,17-dihydroxy-19-desmethylandrostane-9-en-3, 20-dione bis (1, 2-ethanediol) cyclic acetal is an intermediate of ulipristal acetate. Ulipristal acetate is a progesterone agonist/antagonist whose primary action is to inhibit or delay ovulation. Ulipristal acetate is a selective progesterone receptor modulator with antagonistic and partial agonistic effects on progesterone receptors. |
| preparation | The first step: 3-methoxy-19-norpregn-1, 3,4(10) oxidation reaction with 17(20)-tetraene to prepare 3-methoxy-19-norpregnane-1, 3,5(10)-trien-17α; Second step: add 3-methoxy-19-norpregnane-1, 3,5(10)-Trien-17α is reduced with 20 α-diol to produce 3-methoxy-19-norpregnane-2, 5(10)-dien-17α, 20 α-diol; The third step: 3-methoxy-19-norprogestin -2,5(10)-diene -17 alpha, 20 α-diol and oxalic acid are acidified to obtain 17 α,20 α-dihydroxy-19-nor-5 (10)-pregnenol-3-one. Step 4: bromination of 17 α,20 α-dihydroxy-19-nor-5 (10)-pregnane-3-one via pyridinium hydrobromide to give 17 α,20 α-dihydroxy-19-norprogestin -4, 9-dien-3-one; Fifth step: 17 α,20 α-dihydroxy-19-norpregnane-4, 9-BIS The corresponding 17 α-hydroxy-19-norpregnane-4, 9-diene-3, 20-dione was obtained by The chloro-oxidation of en-3-one with ethylene glycol in dimethyl sulfoxide; the sixth step: 17 α-hydroxy-19-norprogestin -4, 9-diene-3, 20-dione is protected with ethylene glycol diketal to react to form 3,3,20, 20-bis (ethylenedioxy) -19-norpregnase-5 (10),9 (11)-dien-17 α-ol; Step 7: 3,3,20,20-bis (ethylenedioxy)-19-norprogestin -5(10),9 (11) with M-chloroperoxybenzoic acid oxidation of-dien-17 α-alcohol to 5 α,10 α-epoxy-3, 3,20, 20-bis (ethylenedioxy)-19-(11)-ethylene-17 α-alcohol; Step 8: 5 α,10 α-epoxy-3, 3,20, 20-bis (ethylenedioxy) -19-norpregnane-9 (11) addition ring opening of-en-17 α-alcohol with 4-dimethylaminobromobenzene by Grignard reagent to obtain (5A,11B)-11-[4-(dimethylamino) phenyl]-5, 17-dihydroxy-19-desmethyl Androstane-9-en-3, 20-dione bis (1, 2-ethanediol) cyclic acetal. |
Last Update：2024-04-09 21:04:16
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