3-Fluoro-4-(methoxycarbonyl)benzeneboronic acid → methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-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

HRID 2405474

反応式

HRID 2405474 の反応式
C[C@]12[C@@]3(C)[C@@H]([C@]4(C)[C@@H](CC3)C(C)(C)C(OS(C(F)(F)F)(=O)=O)=CC4)CC[C@@H]1[C@H]1[C@H](C(C)=C)CC[C@]1(C(O[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=O)CC2.CO[C:50]([C:52]1[CH:57]=C[C:55](C2C(C)(C)[C@H]3[C@](C)(CC=2)[C@@H]2[C@](C)([C@@]4(C)[C@H](CC2)[C@H]2[C@H](C(C)=C)CC[C@]2(C(OCC2C=CC=CC=2)=O)CC4)CC3)=[CH:54][CH:53]=1)=O.[F:97][C:98]1[CH:99]=[C:100](B(O)O)[CH:101]=[CH:102][C:103]=1[C:104]([O:106][CH3:107])=[O:105].[CH3:111]OC(C1C=CC(C2C(C)(C)[C@H]3[C@](C)(CC=2)[C@@H]2[C@](C)([C@@]4(C)[C@H](CC2)[C@H]2[C@H](C(C)=C)CC[C@]2(C(O[Si](C(C)(C)C)(C)C)=O)CC4)CC3)=CC=1)=O.[Cl:160][C:161]([C@:163]12[CH2:198][CH2:197][C@@H:196]([C:199]([CH3:201])=[CH2:200])[C@@H:164]1[C@@H:165]1[C@@:178](C)([CH2:179][CH2:180]2)[C@@:177]2(C)[C@@H]([C@]3(C)[C@@H](CC2)C(C)(C)C(C2C=CC(C(OC)=O)=CC=2)=CC3)[CH2:167][CH2:166]1)=[O:162]>>[Cl:160][C:161]([C@:163]12[CH2:198][CH2:197][C@@H:196]([C:199]([CH3:201])=[CH2:200])[C@@H:164]1[C@@H:165]1[C@@:178]([CH3:177])([CH2:179][CH2:180]2)[C@@:44]2([CH3:111])[C@@H:43]([C@:42]3([CH3:41])[C@@H:47]([CH2:46][CH2:45]2)[C:52]([CH3:57])([CH3:50])[C:53]([C:100]2[CH:101]=[CH:102][C:103]([C:104]([O:106][CH3:107])=[O:105])=[C:98]([F:97])[CH:99]=2)=[CH:54][CH2:55]3)[CH2:167][CH2:166]1)=[O:162]

参加物

6

反応物 5

HCID 27828183-Fluoro-4-(methoxycarbonyl)benzeneboronic acidHCID 54761067(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-benzyl 5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-9-(((trifluoromethyl)sulfonyl)oxy)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate2 回HCID 67776655(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-tert-butyldimethylsilyl 9-(4-(methoxycarbonyl)phenyl)-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]chrysene-3a-carboxylate2 回HCID 67776728(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR 13bR)-benzyl 9-(4-(methoxycarbonyl)phenyl)-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]chrysene-3a-carboxylateHCID 86666171methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-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)benzoate2 回

生成物 1

HCID 86666172methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-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

実験手順

The title compound was prepared from (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-benzyl 5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-9-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate (Intermediate 3) following the above described procedures for the Suzuki coupling (as described for intermediate 4, but using 3-fluoro-4-(methoxycarbonyl)phenylboronic acid as the reactant); deprotection of the C-28 acid (as described for intermediate 5 and 6) and conversion into acid chloride (as described for intermediate 7). The crude material was taken to the next step without further purification. LCMS: m/e 605.39 (M−Cl+OMe+H)+, 4.12 min (method 1).

後処理

  1. customThe crude material was taken to the next step without further purification
  2. customM−Cl+OMe+H)+, 4.12 min (method 1)

出典と根拠

ORDレコード
ord-910521a0de8b433d98e4d911ed41a9c9
出典データセット
uspto-grants-2014_08
特許番号
US08802661B2

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