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N-Methyl dicyclohexylamine → HCID 86731498, 화합물

HRID 1773039
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HRID 1773039 반응식
FC(F)(F)S(O[C:7]1[C:8]([CH3:46])([CH3:45])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:44])([C@@:13]3([CH3:43])[C@H:18]([CH2:19][CH2:20]1)[C@H:17]1[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:16]1([NH:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][S:38](=[O:42])(=[O:41])[CH2:37][CH2:36]1)[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)(=O)=O.[C:49]([O:53][C:54]([NH:56][C:57]1([C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH2:59][CH:58]1[CH:60]=[CH2:61])=[O:55])([CH3:52])([CH3:51])[CH3:50].C1(N(C)C2CCCCC2)CCCCC1>O1CCOCC1.C(OCC)C.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:49]([O:53][C:54]([NH:56][C:57]1([C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH2:59][CH:58]1/[CH:60]=[CH:61]/[C:7]1[C:8]([CH3:46])([CH3:45])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:44])([C@@:13]3([CH3:43])[C@H:18]([CH2:19][CH2:20]1)[C@H:17]1[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:16]1([NH:32][CH2:33][CH2:34][N:35]1[CH2:36][CH2:37][S:38](=[O:42])(=[O:41])[CH2:39][CH2:40]1)[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)=[O:55])([CH3:52])([CH3:50])[CH3:51]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 24210N-Methyl dicyclohexylamineHCID 22091725Ethyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylateHCID 71698666(1R,3aS,5aR,5bR,7aR,11aR,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 trifluoromethanesulfonate

생성물 1

HCID 86731498
HCID 86731498, 화합물

시약·촉매·용매 3

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)촉매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

The mixture of (1R,3aS,5aR,5bR,7aR,11aR,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 trifluoromethanesulfonate (50 mg, 0.070 mmol), ethyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate (17.76 mg, 0.070 mmol) and N-cyclohexyl-N-methylcyclohexanamine (0.018 mL, 0.083 mmol) in dioxane (1 mL) was placed in a sealable pressure tube and N2 was bubbled through the solution for 10 min. Bis(tri-tertbutylphosphine) Palladium(0) (0.355 mg, 0.695 μmol) was added to the reaction mixture and the tube was sealed, and heated to 110° C. for 4 h. After cooling to rt, the crude reaction mixture was diluted with diethyl ether and filtered. The filtrate was concentrated and purified using a flash silica gel column (4 g; eluted with ethyl acetate in hexane from 0 to 45%) to give the title compound as a yellow film (13 mg, 22.7%). MS: m/e 824.55 (M+H)+, 2.625 min (method 4). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.23-5.36 (m, 2H), 5.27-5.12 (m, 1H), 4.72 (br. s., 1H), 4.61 (br. s., 1H), 4.26 (m, 2H), 3.24-2.92 (m, 8H), 2.72-2.45 (m, 5H), 2.32-1.76 (m, 11H), 1.68 (br. s., 3H), 1.53-0.74 (m, 42H).

후처리

  1. customwas placed in a sealable pressure tube
  2. customN2 was bubbled through the solution for 10 min
  3. customthe tube was sealed
  4. temperatureAfter cooling to rt
  5. customthe crude reaction mixture
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified
  9. washa flash silica gel column (4 g; eluted with ethyl acetate in hexane from 0 to 45%)

출처 및 근거

ORD 기록
ord-d99f292f65b640ccb0a97401ad9c2ad8
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249180B2

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