Diisopropylethylamine → tert-butyl N-[(2R,3R)-3-{(2S)-1[(9H-fluoren-9-ylmethoxy)carbonyl]pyrrolidin-2-yl}-3-methoxy-2-methylpropanoyl]-L-phenylalaninate

HRID 74775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74775
Cl.[NH2:2][C@H:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:18]1[C:30]2[CH:29]([CH2:31][O:32][C:33]([N:35]3[CH2:39][CH2:38][CH2:37][C@H:36]3[C@H:40]([O:46][CH3:47])[C@@H:41]([CH3:45])[C:42](O)=[O:43])=[O:34])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C.C(OCC)(=O)C>[CH:27]1[C:28]2[CH:29]([CH2:31][O:32][C:33]([N:35]3[CH2:39][CH2:38][CH2:37][C@H:36]3[C@H:40]([O:46][CH3:47])[C@@H:41]([CH3:45])[C:42]([NH:2][C@H:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:43])=[O:34])[C:30]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]=2[CH:24]=[CH:25][CH:26]=1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)HCID 58078476HCID 58078476, Verbindung

Produkt 1

HCID 86762712tert-butyl N-[(2R,3R)-3-{(2S)-1[(9H-fluoren-9-ylmethoxy)carbonyl]pyrrolidin-2-yl}-3-methoxy-2-methylpropanoyl]-L-phenylalaninateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirring solution of tert-butyl L-phenylalaninate, hydrochloride salt (1.67 g, 6.5 mmol, 1.0 eq.) and #119 (5.9 g, 6.5 mmol, 1.0 eq.) in 50 mL of dichloromethane and 5 mL of DMF, HATU (2.9 g, 7.9 mmol, 1.2 eq.) was added followed by Hunig's base (5.6 mL, 32 mmol, 5.0 eq.). The reaction was allowed to stir at room temperature for 45 minutes. Reaction was reduced down, diluted with ethyl acetate, washed with 0.5 N HCl and brine before being concentrated down onto silica. Silica chromatography was then performed (Gradient: 0%-25% acetone in heptane) producing #120 (3.14 g, 79%) as a white yellow solid. LC-MS (Protocol Q): m/z 613.1 [M+H+] retention time=2.37 minutes.

Aufarbeitung

  1. customReaction
  2. washwashed with 0.5 N HCl and brine
  3. concentrationbefore being concentrated down onto silica

Quellen und Nachweise

ORD-Eintrag
ord-4fc36a71e7de46f78f3daae25ee71b0e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828401B2

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