Trifluoroacetic acid → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(2R,3S,4S)-1-carboxy-2-methoxy-4-methylhexan-3-yl]-N-methyl-L-valinamide

HRID 74783ノート

反応式

HRID 74783 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]([CH3:49])[C:19]([CH3:48])([C:21]([NH:23][C@H:24]([C:28]([N:30]([C@@H:32]([C@@H:44]([CH3:47])[CH2:45][CH3:46])[C@H:33]([O:42][CH3:43])[CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])[CH3:31])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])[CH3:20])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>ClCCl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]([CH3:49])[C:19]([CH3:48])([C:21]([NH:23][C@H:24]([C:28]([N:30]([C@@H:32]([C@@H:44]([CH3:47])[CH2:45][CH3:46])[C@H:33]([O:42][CH3:43])[CH2:34][C:35]([OH:37])=[O:36])[CH3:31])=[O:29])[CH:25]([CH3:26])[CH3:27])=[O:22])[CH3:20])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86685748N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(3R,4S,5S)-1-tert-butoxy-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

生成物 1

HCID 86762713N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(2R,3S,4S)-1-carboxy-2-methoxy-4-methylhexan-3-yl]-N-methyl-L-valinamide収率 99.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirring solution of #127 (4.2 g, 6.1 mmol, 1.0 eq.) in 21 mL of dichloromethane under nitrogen, (7 mL, 90 mmol, 10 eq.) of TFA was added. The reaction was allowed to stir at room temperature for −4 hours. Reaction was concentrated in vacuo, azeotroped once with heptane, and then placed underneath high vacuum yielding #128 as a white slight yellow solid (3.8 g, quant.). LC-MS (Protocol Q): m/z 624.2 [M+H+] retention time=2.01 minutes.

後処理

  1. customReaction
  2. concentrationwas concentrated in vacuo
  3. customazeotroped once with heptane

出典と根拠

ORDレコード
ord-289578c2bdbe4ddb84e0658e4e8c8496
出典データセット
uspto-grants-2014_09
特許番号
US08828401B2

反応ノート

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