1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2R,5S,6S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester

HRID 229828

Reaktionsgleichung

Reaktionsgleichung von HRID 229828
CN(C)CCCN=C=NCC.O.[C:13]([NH:20][C@H:21]([C:26]([OH:28])=O)[CH2:22][CH:23]([CH3:25])[CH3:24])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(N(C(C)C)CC)(C)C.OC1C2N=NNC=2C=CC=1.[CH2:48]([O:55][C:56]([N:58]1[CH2:64][CH:63]([OH:65])[CH:62]([NH2:66])[CH2:61][CH2:60][CH:59]1[CH3:67])=[O:57])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN(C=O)C.CCOC(C)=O>[CH2:48]([O:55][C:56]([N:58]1[CH2:64][C@H:63]([OH:65])[C@@H:62]([NH:66][C:26](=[O:28])[C@@H:21]([NH:20][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:22][CH:23]([CH3:24])[CH3:25])[CH2:61][CH2:60][C@H:59]1[CH3:67])=[O:57])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 12373896N-Boc-L-Leucine HydrateHCID 21036430Racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl esterHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 69000072(2R,5S,6S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl esterAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.164 g, 0.22 mmol) was added to a solution of Boc-Leucine-hydrate (0.190 g, 0.76 mmol), diisopropylethylamine (0.164 g, 0.22 ml, 1.27 mmol), hydroxybenztriazole (0.114 g, 0.83 mmol), and racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.27 g, 0.57 mmol) in DMF (3.2 ml). The reaction was stirred overnight at RT, then was diluted with EtOAc (100 ml), washed with H2O (3×50 ml), brine (50 ml), dried with magnesium sulfate, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 50% EtOAc/hexanes) to yield the title compound (0.218 g, 72%): 1H NMR: 7.40-7.29 (m, 5H), 6.75 (1H, bd), 5.12 (2H, AB), 5.0 (1H, bs), 4.15-3.72 (m, 2H), 3.06 (1H, d), 1.60-1.30 (m, 2H), 1.60-1.30 (m, 5H), 1.12 (3H, d), 0.97-0.87(6H, dd); Electrospray mass spec: M+H+=492.0

Aufarbeitung

  1. washwashed with H2O (3×50 ml), brine (50 ml)
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo by rotary evaporation
  5. customchromatographed (silica gel, 50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0fdf3ab416f44090b08fe9c0481bf0cb
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563784B2

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