Triacetoxyperiodinane → 4-(4-isopropylpiperazin-1-yl)-N-((S)-1-((3aS,6R,6aS)-6-methoxy-3-oxodihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethyl-1-oxopentan-2-yl)benzamide

HRID 1716469노트

반응식

HRID 1716469 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][C@@H:24]1[C@H:28]2[N:29]([C:34](=[O:59])[C@@H:35]([NH:41][C:42](=[O:58])[C:43]3[CH:48]=[CH:47][C:46]([N:49]4[CH2:54][CH2:53][N:52]([CH:55]([CH3:57])[CH3:56])[CH2:51][CH2:50]4)=[CH:45][CH:44]=3)[CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30][C@@H:31]([O:32][CH3:33])[C@H:27]2[O:26][CH2:25]1>ClCCl>[CH:55]([N:52]1[CH2:51][CH2:50][N:49]([C:46]2[CH:45]=[CH:44][C:43]([C:42]([NH:41][C@@H:35]([CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:34]([N:29]3[CH2:30][C@@H:31]([O:32][CH3:33])[C@H:27]4[O:26][CH2:25][C:24](=[O:23])[C@@H:28]34)=[O:59])=[O:58])=[CH:48][CH:47]=2)[CH2:54][CH2:53]1)([CH3:57])[CH3:56]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 68510175N-((S)-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethyl-1-oxopentan-2-yl)-4-(4-isopropylpiperazin-1yl)benzamide

생성물 1

HCID 250068914-(4-isopropylpiperazin-1-yl)-N-((S)-1-((3aS,6R,6aS)-6-methoxy-3-oxodihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethyl-1-oxopentan-2-yl)benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Dess-Martin periodinane (2.82 g, 6.66 mmol) was added to a stirred solution of N—((S)-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethyl-1-oxopentan-2-yl)-4-(4-isopropylpiperazin-1yl)benzamide (1.72 g, 3.33 mmol) in dichloromethane (65 mL) under an atmosphere of argon. The mixture was stirred for 18 hours then diluted with dichloromethane (300 mL). The organic phase was washed with aqueous sodium hydroxide solution (1M, 100 mL) then the aqueous extracted with dichloromethane (150 mL). The organic layer was washed with aqueous sodium hydroxide solution (1M, 100 mL) then brine (150 mL), then dried (Na2SO4), filtered and reduced in vacuo to give 4-(4-isopropylpiperazin-1-yl)-N—((S)-1-((3aS,6R,6aS)-6-methoxy-3-oxodihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethyl-1-oxopentan-2-yl)benzamide a pale yellow solid (1.408 g, 82%). TLC (Rf=0.45, MeOH:CH2Cl2 1:19), analytical HPLC main peak, Rt=10.39 min., HPLC-MS 515.3 [M+H]+, 533.3 [M+H2O+H]+, 1051.6 [2M+Na]+; [□]D22−31.08° (c=3.7, CHCl3); δH (500 MHz, CDCl3) 0.99 (9H, s, C(CH3)3), 1.08 (6H, d, J=6.52 Hz, NCH(CH3)2), 1.68-1.74 (2H, m, CH2C(CH3)3), 2.65 (4H, brt, J=5.04 Hz, CH2NCH(CH3)2), 2.67-2.73 (1H, m, NCH(CH3)2), 3.29 (4H, brt, J=5.05 Hz, CH2CH2NCH(CH3)2), 3.49 (3H, s, OCH3), 3.61 (1H, dd, 5.35 Hz, NCH2CHOCH3), 4.00-4.04 (1H, m, CHOCH3), 4.09 (1H, d, J=16.89 Hz, OCH2C═O), 4.20 (1H, d, J=16.93 Hz, OCH2C═O), 4.27 (1H, dd, 5.88 Hz, NCH2CHOCH3), 4.74 (1H, d, J=6.86 Hz, OCH2(C═O)CH), 4.91 (1H, dd, 4.28 Hz, OCHCHOCH3), 4.94-5.00 (1H, m, CHCH2C(CH3)3), 6.61 (1H, d, J=8.69 Hz, NH), 6.84 (2H, brd, J=8.95 Hz, aromatic CH), 7.65 (2H, brd, J=8.91 Hz, aromatic CH); δC (125 MHz, CDCl3) 18.53 (NCH(CH3)2), 29.75/29.80 (C(CH3)3), 30.75/30.77 (C(CH3)3), 46.53 (CH2C(CH3)3), 47.02 (NCH2CH2NCH(CH3)2), 48.24 (CHCH2C(CH3)3), 48.43 (NCH2CH2NCH(CH3)2), 49.76 (NCH2CHOCH3), 54.49 (NCH(CH3)2), 58.23 (OCH3), 60.49 (OCH2C(═O)CH), 71.45 (OCH2C═O), 78.84 (CHOCH3), 80.25 (OCHCHOCH3), 114.01/114.10/128.49 and 129.83 (aromatic CH), 123.08 (aromatic quaternary), 153.55 (aromatic quaternary), 166.69 (NHC═O), 173.53 (CH2NC═O), 207.93 (ketone C═O).

후처리

  1. washThe organic phase was washed with aqueous sodium hydroxide solution (1M, 100 mL)
  2. extractionthe aqueous extracted with dichloromethane (150 mL)
  3. washThe organic layer was washed with aqueous sodium hydroxide solution (1M, 100 mL)
  4. dry with materialbrine (150 mL), then dried (Na2SO4)
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-11804fe727b04256a41a1c298bac0a3c
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803803B2

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