Trifluoroacetic acid → HCID 71596818, 화합물

HRID 405065노트

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HRID 405065 반응식
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]([CH3:59])([CH3:58])[C@H:16]3[C@:29]([CH3:32])([CH2:30][CH:31]=2)[C@@H:28]2[C@:19]([CH3:57])([C@@:20]4([CH3:56])[C@H:25]([CH2:26][CH2:27]2)[C@H:24]2[C@H:33]([C:36]([CH3:38])=[CH2:37])[CH2:34][CH2:35][C@:23]2([CH2:39][NH:40][CH2:41][CH2:42][N:43]2[CH2:48][CH2:47][N:46](C(OC(C)(C)C)=O)[CH2:45][CH2:44]2)[CH2:22][CH2:21]4)[CH2:18][CH2:17]3)=[CH:10][CH:9]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:56][C@:20]12[C@@:19]3([CH3:57])[C@@H:28]([C@:29]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:58])([CH3:59])[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:6]([OH:7])=[O:5])=[CH:9][CH:10]=3)=[CH:31][CH2:30]4)[CH2:27][CH2:26][C@@H:25]1[C@H:24]1[C@H:33]([C:36]([CH3:38])=[CH2:37])[CH2:34][CH2:35][C@:23]1([CH2:39][NH:40][CH2:41][CH2:42][N:43]1[CH2:44][CH2:45][NH:46][CH2:47][CH2:48]1)[CH2:22][CH2:21]2

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86676406tert-butyl 4-(2-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(tert-butoxycarbonyl)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]chrysen-3a-yl)methylamino)ethyl)piperazine-1-carboxylate

생성물 1

HCID 71596818HCID 71596818, 화합물수율 16.43%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 4-(2-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(tert-butoxycarbonyl)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]chrysen-3a-yl)methylamino)ethyl)piperazine-1-carboxylate (136 mg, 0.167 mmol) in DCM (1 ml) was added TFA (0.4 ml, 5.19 mmol). The mixture was stirred at rt for 5 h then was concentrated under reduced pressure. The residue was dissolved in dioxane and MeOH and was purified by prep. HPLC. The fractions containing the expected product were combined and concentrated under reduced pressure. HPLC showed some impurities were still present, so the reaction was repurified by prep. HPLC. The fractions were concentrated under reduced pressure to give the title compound as a white solid (18 mg, 0.027 mmol, 16.43% yield). LCMS: m/e 656.6 (M+H)+, 2.24 min (method 6). 1H NMR (500 MHz, Acetic) δ ppm 8.03 (d, J=8.24 Hz, 2H),7.30 (d, J=8.24 Hz, 2H), 5.37 (d, J=4.58 Hz, 1H), 4.79 (s, 1H), 4.68 (s, 1H), 3.50-3.67 (m, 6H), 3.40 (d, J=12.82 Hz, 1H), 3.22-3.29 (m, 6H), 2.99 (d, J=13.12 Hz, 1H), 2.49-2.58 (m, 1H), 1.76 (s, 3H), 1.19 (s, 3H), 1.16-2.23 (m, 22H), 1.10 (s, 3H), 1.08 (s, 3H), 1.02 (s, 3H), 1.00 (s, 3H).

후처리

  1. concentrationthen was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dioxane
  3. customMeOH and was purified by prep
  4. additionThe fractions containing the expected product
  5. concentrationconcentrated under reduced pressure
  6. customwas repurified by prep
  7. concentrationThe fractions were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-516667716d1d4258bcde7172e67bc494
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748415B2

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