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Acetic Acid → (2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methyl-N-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}pentanamide

HRID 1092620
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HRID 1092620 반응식
[O:1]=[S:2]1(=[O:23])[CH2:6][CH2:5][CH2:4][N:3]1[C@@H:7]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:8]([NH:10][C@H:11]1[C@H:18]2[C@H:14]([CH2:15][NH:16][CH2:17]2)[CH2:13][CH2:12]1)=[O:9].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O.C(O)(=O)C.C([BH3-])#N>ClCCl>[O:23]=[S:2]1(=[O:1])[CH2:6][CH2:5][CH2:4][N:3]1[C@@H:7]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:8]([NH:10][C@H:11]1[C@H:18]2[C@H:14]([CH2:15][N:16]([CH2:29][C:28]3[CH:31]=[CH:32][CH:33]=[C:26]([C:25]([F:24])([F:34])[F:35])[CH:27]=3)[CH2:17]2)[CH2:13][CH2:12]1)=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 679903-(Trifluoromethyl)benzaldehydeHCID 498716Cyano-borohydrideHCID 66590695(2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methyl-N-[(3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]pentanamide

생성물 1

HCID 66590670(2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methyl-N-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}pentanamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(2S)-2-(1,1-Dioxidoisothiazolidin-2-yl)-4-methyl-N-[(3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]pentanamide (204 mg, 0.594 mmol) and 3-(trifluoromethyl)benzaldehyde (0.158 mL, 1.188 mmol) were dissolved in dichloromethane (3 mL). Acetic acid (1 mL) was added. The reaction was stirred at ambient temperature for 20 min, then PS-cyanoborohydride (487 mg, 1.188 mmol) was added. The reaction was stirred at room temperature overnight, then filtered, and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane to the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.79 (d, J=7.0, 1H), 7.75 (d, J=10.3, 1H), 7.61-7.54 (m, 2H), 7.44 (t, J=7.7, 1H), 4.52 (dd, J=6.6, 8.9, 1H), 4.38 (dq, J=6.4, 12.6, 1H), 3.94 (dd, J=7.3, 16.2, 1H), 3.57 (dd, J=9.1, 13.5, 1H), 3.50-3.37 (m, 2H), 3.31-3.19 (m, 2H), 2.79 (ddd, J=3.0, 9.1, 19.0, 1H), 2.62-2.54 (m, 1H), 2.54-2.45 (m, 1H), 2.43-2.36 (m, 1H), 2.31-2.16 (m, 4H), 2.13-2.03 (m, 1H), 1.94-1.78 (m, 3H), 1.77-1.59 (m, 2H), 1.39 (dt, J=6.5, 19.8, 1H), 0.88 (d, J=6.6, 3H), 0.82 (dd, J=2.3, 6.5, 3H); MS (ESI+) m/z 502 (M+H)+.

후처리

  1. stirringThe reaction was stirred at room temperature overnight
  2. filtrationfiltered
  3. customthe solvent was removed in vacuo
  4. customThe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-e28b3987e6c5423a93bd5228947d762b
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129417B2

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