Hydrochloric Acid → methyl 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)-2-fluorobenzoate dihydrochloride

HRID 85692ノート

反応式

HRID 85692 の反応式
[F:1][C:2]1[CH:11]=[C:10]([C:12]2[C:13]([CH3:43])([CH3:42])[C@H:14]3[C@:27]([CH3:30])([CH2:28][CH:29]=2)[C@@H:26]2[C@:17]([CH3:41])([C@@:18]4([CH3:40])[C@H:23]([CH2:24][CH2:25]2)[C@H:22]2[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:21]2([N:37]=C=O)[CH2:20][CH2:19]4)[CH2:16][CH2:15]3)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[ClH:44]>C1COCC1.O>[ClH:44].[ClH:44].[NH2:37][C@:21]12[CH2:33][CH2:32][C@@H:31]([C:34]([CH3:36])=[CH2:35])[C@@H:22]1[C@@H:23]1[C@@:18]([CH3:40])([CH2:19][CH2:20]2)[C@@:17]2([CH3:41])[C@@H:26]([C@:27]3([CH3:30])[C@@H:14]([CH2:15][CH2:16]2)[C:13]([CH3:42])([CH3:43])[C:12]([C:10]2[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=2)=[CH:29][CH2:28]3)[CH2:25][CH2:24]1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 86676622methyl 2-fluoro-4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-isocyanato-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)benzoate

生成物 1

HCID 86762805methyl 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)-2-fluorobenzoate dihydrochloride収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of crude methyl 2-fluoro-4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-isocyanato-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)benzoate (2.93 g, 4.99 mmol) in THF (35 mL) was added 12N HCl (10 mL, 121 mmol). After stirring the mixture for 24 h, the mixture was diluted with water (100 mL) until solids precipitated. The solids were collected by filtration and were washed with water to afford the title compound (2.75 g, 4.33 mmol, 87% yield), as an off-white solid that was used in the next step with no additional purification. LCMS: m/e 562 (M+H)+, 1.96 min (method 2).

後処理

  1. customprecipitated
  2. filtrationThe solids were collected by filtration
  3. washwere washed with water

出典と根拠

ORDレコード
ord-256d1e6c3c5c4c50b1b11a7fecfd533c
出典データセット
uspto-grants-2014_09
特許番号
US08846647B2

反応ノート

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