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Phosphoric Acid → ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methylene)cyclohexanecarboxylate

HRID 1773037
ノート
印刷プレビュー

反応式

HRID 1773037 の反応式
[NH2:1][C@:2]12[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:36])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([CH:24]=[C:25]2[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1.P(=O)(O)(O)O.[K].[I-].[K+].Cl[CH2:52][CH2:53][N:54]1[CH2:59][CH2:58][S:57](=[O:61])(=[O:60])[CH2:56][CH2:55]1>C(#N)C>[O:60]=[S:57]1(=[O:61])[CH2:58][CH2:59][N:54]([CH2:53][CH2:52][NH:1][C@:2]23[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:3]2[C@@H:4]2[C@@:17]([CH3:20])([CH2:18][CH2:19]3)[C@@:16]3([CH3:21])[C@@H:7]([C@:8]4([CH3:36])[C@@H:13]([CH2:14][CH2:15]3)[C:12]([CH3:22])([CH3:23])[C:11]([CH:24]=[C:25]3[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]3)=[CH:10][CH2:9]4)[CH2:6][CH2:5]2)[CH2:55][CH2:56]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 1004Phosphoric AcidHCID 4875Potassium IodideHCID 5462222PotassiumHCID 189487894-(2-chloroethyl)thiomorpholine1,1-dioxideHCID 86731496HCID 86731496、化合物

生成物 1

HCID 86731495
ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methylene)cyclohexanecarboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

To a sealable flask containing ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methylene)cyclohexanecarboxylate (0.015 g, 0.026 mmol) was added phosphoric acid, potassium salt (0.028 g, 0.130 mmol), potassium iodide (0.013 g, 0.078 mmol) and 4-(2-chloroethyl)thiomorpholine 1,1-dioxide (0.015 g, 0.078 mmol). The mixture was diluted with acetonitrile (1 mL), flushed with nitrogen, sealed, and heated to 100° C. After heating the mixture for 22 h, it was cooled to rt, diluted with water (5 mL), and extracted with dichloromethane (3×5 mL). The organic layers were dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was used in the next step with no additional purification. LCMS: m/e: 737.7 (M+H)1, 2.22 min (method 1).

後処理

  1. customflushed with nitrogen
  2. customsealed
  3. temperatureAfter heating the mixture for 22 h
  4. temperatureit was cooled to rt
  5. additiondiluted with water (5 mL)
  6. extractionextracted with dichloromethane (3×5 mL)
  7. dry with materialThe organic layers were dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was used in the next step with no additional purification
  11. custom737.7 (M+H)1, 2.22 min (method 1)

出典と根拠

ORDレコード
ord-e0ea9513bcd1460ca5778d143be87c28
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09249180B2

反応ノート

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