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 74783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74783
[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

Komponenten

4

Edukt 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

Produkt 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-valinamideAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-289578c2bdbe4ddb84e0658e4e8c8496
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828401B2

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