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Sodium Hydroxide → HCID 50923385, 화합물

HRID 2179803
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HRID 2179803 반응식
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:48])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:47])[CH2:12][CH2:13][C@@:14]3([C:30](=[O:46])[NH:31][C@@H:32]4[CH2:35][C@H:34]([C:36]([N:38]5[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]5)=[O:37])[C:33]4([CH3:45])[CH3:44])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:50])[CH3:49])(=O)C.[OH-].[Na+]>CO.C1COCC1>[CH3:44][C:33]1([CH3:45])[C@@H:34]([C:36]([N:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)=[O:37])[CH2:35][C@H:32]1[NH:31][C:30]([C@:14]12[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]1[C@@H:16]1[C@@:11]([CH3:47])([CH2:12][CH2:13]2)[C@@:10]2([CH3:48])[C@@H:19]([C@:20]3([CH3:23])[C@@H:7]([CH2:8][CH2:9]2)[C:6]([CH3:49])([CH3:50])[C@@H:5]([OH:4])[CH2:22][CH2:21]3)[CH2:18][CH2:17]1)=[O:46]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 50923384HCID 50923384, 화합물

생성물 1

HCID 50923385HCID 50923385, 화합물수율 74.6%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1R,3S)-2,2-dimethyl-3-(piperidine-1-carbonyl)cyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl acetate (Example 46, 0.400 g, 0.579 mmol) in MeOH:THF (2:1) (30 ml) 2N NaOH (10 ml) was added at 0° C. and allowed to stir at room temperature for about 16 hours. After completion of the reaction (monitored by TLC), the volatile was evaporated and the aqueous layer was extracted with ethyl acetate and the organic layer was washed with water, brine and dried over Na2SO4 then the solvent was evaporated and the resulting crude stirred in hexane and the resulting solid was obtained which was filtered and dried under vacuum to afford the title compound. Wt: 0.280 g; Yield: 74.6%; 1H NMR (300 MHz, CDCl3): δ 5.86 (d, 1H, J=8.1 Hz), 4.72 (s, 1H), 4.57 (s, 1H), 4.18-4.06 (m, 1H), 3.78-3.68 (m, 1H), 3.52-3.30 (m, 3H), 3.23-3.08 (m, 2H), 2.92-2.86 (m, 1H), 2.52-2.20 (m, 3H), 2.01-1.88 (m, 2H), 1.80-1.12 (m, 33H), 0.96, 0.93, 0.87, 0.81, 0.74 (s, 18H); Mass: [M+1]+ 649 (5%), [M+Na]+ 671 (100%); IR (KBr, cm−1): 3353, 2937, 2858, 1635, 1618, 1533, 1459, 1390, 1262, 1250, 1148, 1048, 1033, 1020, 983, 883; M.R: 177° C.-188.7° C.; HPLC: 95.72%.

후처리

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe volatile was evaporated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated
  7. stirringthe resulting crude stirred in hexane
  8. customthe resulting solid was obtained which
  9. filtrationwas filtered
  10. customdried under vacuum

출처 및 근거

ORD 기록
ord-94f3fe23aa174d5183dd77ccf172f34a
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067966B2

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