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 2282849ノート

反応式

HRID 2282849 の反応式
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]

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bf7b41a840d745b9bf6db6e5996d8687
出典データセット
uspto-grants-2015_09
特許番号
US09138486B2

反応ノート

読み込み中…