126690-41-3

126690-41-3 - Names and Identifiers

Name	(5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal)
Synonyms	3,20-bis-ethylenedioxy-5,17-dihydroxy-11-(4-N,N-dimethylaminophenyl)-19-norpregn-9-ene 3,20-BIS-ETHYLENEDIOXY-5Α,17Α-DIHYDROXY-11Β-(4-N,N-DIMETHYLAMINOPHENYL)-19-NORPREGN-9-ENE 3,3,20,20-Bis(ethylene-dioxy) -5α, 17α-dihydroxy-11β- 4-(N,N-diMethylaMino) -phenyl -19-norpregna-9(11)-ene 3,3,3,20,20-Bis(ethylene-dioxy) -5α,17α-dihydroxy-11β-[4-(N, N-diMethylaMino)-phenyl]-19-norpregna-9(11)-ene (5α,11β)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclicbis(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) 3,3,3,20,20-Bis(ethylene-dioxy) -5alpha,17alpha-dihydroxy-11beta-[4-(N, N-diMethylaMino)-phenyl]-19-norpregna-9(11)-ene (5alpha,11beta)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal)
CAS	126690-41-3
EINECS	1592732-453-0

126690-41-3 - 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)

126690-41-3 - 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