Trifluoroacetic acid → 4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[2-dimethylaminoethyl-(3-hydroxy-3-oxo-propanoyl)amino]methyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid

HRID 405071ノート

反応式

HRID 405071 の反応式
C([O:5][C:6](=[O:59])[CH2:7][C:8]([N:10]([CH2:16][C@:17]12[CH2:55][CH2:54][C@@H:53]([C:56]([CH3:58])=[CH2:57])[C@@H:18]1[C@@H:19]1[C@@:32]([CH3:35])([CH2:33][CH2:34]2)[C@@:31]2([CH3:36])[C@@H:22]([C@:23]3([CH3:52])[C@@H:28]([CH2:29][CH2:30]2)[C:27]([CH3:38])([CH3:37])[C:26]([C:39]2[CH:51]=[CH:50][C:42]([C:43]([O:45]C(C)(C)C)=[O:44])=[CH:41][CH:40]=2)=[CH:25][CH2:24]3)[CH2:21][CH2:20]1)[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[O:9])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:6]([CH2:7][C:8]([N:10]([CH2:16][C@:17]12[CH2:55][CH2:54][C@@H:53]([C:56]([CH3:58])=[CH2:57])[C@@H:18]1[C@@H:19]1[C@@:32]([CH3:35])([CH2:33][CH2:34]2)[C@@:31]2([CH3:36])[C@@H:22]([C@:23]3([CH3:52])[C@@H:28]([CH2:29][CH2:30]2)[C:27]([CH3:38])([CH3:37])[C:26]([C:39]2[CH:40]=[CH:41][C:42]([C:43]([OH:45])=[O:44])=[CH:50][CH:51]=2)=[CH:25][CH2:24]3)[CH2:21][CH2:20]1)[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[O:9])([OH:59])=[O:5]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86676409tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-tert-butoxy-N-(2-(dimethylamino)ethyl)-3-oxopropanamido)methyl)-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 715964874-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[2-dimethylaminoethyl-(3-hydroxy-3-oxo-propanoyl)amino]methyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid収率 56.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-tert-butoxy-N-(2-(dimethylamino)ethyl)-3-oxopropanamido)methyl)-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 (31 mg, 0.038 mmol) in dichloromethane (1 ml) was added TFA (0.25 ml, 3.24 mmol). The mixture was stirred at rt for 3 h then was concentrated under reduced pressure. The residue was purified by prep HPLC. The fractions containing the expected product were combined and concentrated under reduced pressure to afford 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-carboxy-N-(2-(dimethylamino)ethyl)acetamido)methyl)-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)benzoic acid as a white solid (15 mg, 0.021 mmol, 56.1% yield). LCMS: m/e 701.5 (M+H)+, 2.11 min (method 6). 1H NMR (500 MHz, Acetic acid-d3 acid-d) δ ppm 8.04 (d, J=8.24 Hz, 2H), 7.31 (d, J=8.24 Hz, 2H), 5.38 (d, J=5.19 Hz, 1H), 4.85 (d, J=16.17 Hz, 1H), 4.69 (d, J=15.56 Hz, 1H), 3.86-4.13 (m, 2H), 2.97-3.82 (m, 6H), 2.62-2.73 (m, 1H), 2.13-2.24 (m, 2H), 1.06-1.92 (m, 38H), 1.03 (s, 3H), 1.01 (s, 3H).

後処理

  1. concentrationthen was concentrated under reduced pressure
  2. customThe residue was purified by prep HPLC
  3. additionThe fractions containing the expected product
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-8fcf456288ed4a03bfb36e3b4cf95201
出典データセット
uspto-grants-2014_06
特許番号
US08748415B2

反応ノート

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