Trifluoroacetic acid → N,2-dimethylalanyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

HRID 2282849노트

반응식

HRID 2282849 반응식
C(O[C:6]([N:8](C)[C:9]([CH3:59])([C:11]([NH:13][C@H:14]([C:18]([N:20]([C@@H:22]([C@@H:55]([CH3:58])[CH2:56][CH3:57])[C@H:23]([O:53][CH3:54])[CH2:24][C:25]([N:27]1[CH2:31][CH2:30][CH2:29][C@H:28]1[C@H:32]([O:51][CH3:52])[C@@H:33]([CH3:50])[C:34](=[O:49])[NH:35][C@H:36]([C:44]1[S:45][CH:46]=[CH:47][N:48]=1)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:26])[CH3:21])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH3:10])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:6][NH:8][C:9]([CH3:59])([C:11]([NH:13][C@H:14]([C:18]([N:20]([C@@H:22]([C@@H:55]([CH3:58])[CH2:56][CH3:57])[C@H:23]([O:53][CH3:54])[CH2:24][C:25]([N:27]1[CH2:31][CH2:30][CH2:29][C@H:28]1[C@H:32]([O:51][CH3:52])[C@@H:33]([CH3:50])[C:34](=[O:49])[NH:35][C@H:36]([C:44]1[S:45][CH:46]=[CH:47][N:48]=1)[CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:26])[CH3:21])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH3:10]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86685737N-(tert-butoxycarbonyl)-N,2-dimethylalanyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

생성물 1

HCID 86685738N,2-dimethylalanyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of #87 (58 mg, 0.068 mmol, 1 eq.) in dichloromethane (8 mL) was added trifluoroacetic acid (2 mL). After stirring overnight, the reaction mixture was concentrated in vacuo. The residue was taken up in ethyl acetate (10 mL), washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered, and concentrated in vacuo to give #88 (52 mg, quantitative). LC-MS 757.6 [M+H+], retention time=0.69 minute; 1H NMR (400 MHz, DMSO-d6), presumed to be a mixture of rotamers, characteristic signals: δ [8.64 (br d, J=8.6 Hz) and 8.87 (br d, J=8.6 Hz), total 1H], 7.80-7.85 (m, 1H), [7.77 (d, J=3.3 Hz) and 7.80 (d, J=3.1 Hz), total 1H], [7.63 (d, J=3.1 Hz) and 7.66 (d, J=3.3 Hz), total 1H], 7.20-7.31 (m, 4H), 7.13-7.19 (m, 1H), [5.39 (ddd, J=11, 8.5, 4 Hz) and 5.49-5.56 (m), total 1H], [4.51 (dd, J=9, 8 Hz) and 4.61 (dd, J=9, 8 Hz), total 1H], 3.16, 3.20, 3.21 and 3.25 (4 s, total 6H), 2.94 and 3.03 (2 br s, total 3H), 2.10 and 2.10 (2 s, total 3H), 1.16 (br s, 3H), 1.04-1.12 (m, 6H), 0.72-0.80 (m, 3H).

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give #88 (52 mg, quantitative)
  7. additiona mixture of rotamers, characteristic signals

출처 및 근거

ORD 기록
ord-bf7b41a840d745b9bf6db6e5996d8687
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09138486B2

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