Methyl Acrylate → dimethyl 3,3'-(2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-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-carboxamido)ethylazanediyl)dipropanoate

HRID 2405495노트

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HRID 2405495 반응식
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C@:7]12[CH2:42][CH2:41][C@@H:40]([C:43]([CH3:45])=[CH2:44])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:39])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:28])([CH3:27])[C:16]([C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)=[O:6].[C:46]([O:50][CH3:51])(=[O:49])[CH:47]=[CH2:48]>CO>[CH3:36][O:35][C:33]([C:32]1[CH:31]=[CH:30][C:29]([C:16]2[C:17]([CH3:27])([CH3:28])[C@H:18]3[C@:13]([CH3:39])([CH2:14][CH:15]=2)[C@@H:12]2[C@:21]([CH3:26])([C@@:22]4([CH3:25])[C@H:9]([CH2:10][CH2:11]2)[C@H:8]2[C@H:40]([C:43]([CH3:45])=[CH2:44])[CH2:41][CH2:42][C@:7]2([C:5]([NH:4][CH2:3][CH2:2][N:1]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:48][CH2:47][C:46]([O:50][CH3:51])=[O:49])=[O:6])[CH2:24][CH2:23]4)[CH2:20][CH2:19]3)=[CH:38][CH:37]=1)=[O:34]

참가 물질

4

반응물 2

HCID 7294Methyl Acrylate2회HCID 67776312methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-aminoethylcarbamoyl)-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

생성물 1

HCID 67774882dimethyl 3,3'-(2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-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-carboxamido)ethylazanediyl)dipropanoate수율 192.5%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
20 °C

실험 절차

A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-aminoethylcarbamoyl)-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 (20 mg, 0.033 mmol) and methyl acrylate (8.40 mg, 0.098 mmol) in methanol (1 mL) was stirred at 20° C. for 3 hours. LCMS indicated the mono-substitution. Methyl acrylate (8.40 mg, 0.098 mmol) was added to the reaction mixture again. The reaction mixture was stirred for 16 hours. The reaction mixture was quenched with distilled water, extracted with DCM (3×3 mL). All the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a white solid (25 mg, 98%). LCMS: m/e 787.48 (M+H)+, 2.67 min (method 1).

후처리

  1. stirringThe reaction mixture was stirred for 16 hours
  2. customThe reaction mixture was quenched with distilled water
  3. extractionextracted with DCM (3×3 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cef122a78f3c49709a8b94aa99353205
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802661B2

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