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

HRID 485631

反応式

HRID 485631 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6101p-Toluenesulfonic acid触媒HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e7e69e196eed439799cadfb1ea32de52
出典データセット
uspto-grants-1985_08
特許番号
US04537722

関連ノート

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