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

HRID 485631

반응식

HRID 485631 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6101p-Toluenesulfonic acid촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e7e69e196eed439799cadfb1ea32de52
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04537722

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