Acetic Acid → (17beta)-17-(3-(4-(Hexyloxy)phenyl)-1-oxopropoxy)estr-4-en-3-one

HRID 485631

Reaktionsgleichung

Reaktionsgleichung von HRID 485631
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@H:20]([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.[CH2:21]([O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36](O)=[O:37])=[CH:30][CH:29]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:11][C@@H:10]2[C@@:2]3([CH3:1])[CH2:3][CH2:4][C@@H:5]4[C@@H:20]5[C:14](=[CH:15][C:16]([CH2:18][CH2:19]5)=[O:17])[CH2:13][CH2:12][C@H:6]4[C@@H:7]3[CH2:8][CH2:9]2)=[O:37])=[CH:30][CH:29]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 9904NandroloneHCID 10868DicyclohexylcarbodiimideHCID 912873-[4-(Hexyloxy)phenyl]propanoic acid

Produkt 1

HCID 92341(17beta)-17-(3-(4-(Hexyloxy)phenyl)-1-oxopropoxy)estr-4-en-3-oneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 5.48 g 19-nortestosterone (20 mmol), 5.5 g 3-(4-hexyloxyphenyl)propionic acid (22 mmol), 0.24 g 4-dimethylaminopyridine (DMAP, 2 mmol) and 0.19 g p-toluenesulfonic acid (pTSA, 1 mmol) in 50 ml CH2Cl2 is slowly added at about 15° C. a solution of 5.2 g N,N'-dicyclohexylcarbodiimide (DCC, 25 mmol) in 30 ml CH2CL2. After 4 h at room temperature (no discolouration of the reaction mixture is seen) 1 ml of acetic acid is added to destroy the excess of DCC. Precipitated urea is then filtered off and the filtrate evaporated in vacuo. To the residue 50 ml ethyl acetate is added and, after stirring for 1 h, undissolved urea is filtered off and the filtrate evaporated in vacuo. The residue is crystallized from methanol/water. There is obtained 9.4 g of Anadur® (93% yield) as white crystals having a m.p. of 53°-55° C. and being pure in TLC.

Aufarbeitung

  1. customto destroy the excess of DCC
  2. filtrationPrecipitated urea is then filtered off
  3. customthe filtrate evaporated in vacuo
  4. additionTo the residue 50 ml ethyl acetate is added
  5. filtrationundissolved urea is filtered off
  6. customthe filtrate evaporated in vacuo
  7. customThe residue is crystallized from methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-e7e69e196eed439799cadfb1ea32de52
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04537722

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