Diisopropylethylamine → 6-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid ethyl ester

HRID 417729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417729
[CH3:1][O:2][C:3]([NH:5][CH:6]([CH:10]([CH3:12])[CH3:11])[C:7]([OH:9])=O)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:37]([O:39][C:40]([CH:42]1[CH2:49][C:45]2([CH2:48][CH2:47][CH2:46]2)[O:44][NH:43]1)=[O:41])[CH3:38].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH2:37]([O:39][C:40]([CH:42]1[CH2:49][C:45]2([CH2:46][CH2:47][CH2:48]2)[O:44][N:43]1[C:7](=[O:9])[CH:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:10]([CH3:12])[CH3:11])=[O:41])[CH3:38]

Komponenten

7

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 138211012-((Methoxycarbonyl)amino)-3-methylbutanoic acidHCID 59611538Ethyl 5-oxa-6-azaspiro[3.4]octane-7-carboxylate

Produkt 1

HCID 666206496-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid ethyl esterAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-methoxycarbonylamino-3-methyl-butyric acid (1.11 g, 6.33 mmol) and HATU (2.41 g, 6.34 mmol) in dimethylformamide (13 mL) was added a solution of 5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid ethyl ester (980 mg, 5.3 mmol) in dimethylformamide (13 mL). To the resulting reaction mixture was added diisopropylethylamine (1.85 mL, 10.6 mmol) and the reaction was heated to 60° C. for 16 hours. The reaction was diluted with ethyl acetate, washed with water and brine, dried (MgSO4) and concentrated. The resulting residue was purified by flash chromatography to give 6-(2-methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid ethyl ester (1.31 g, 72%). LCMS-ESI+: calculated for C16H26N2O6: 342.18; observed [M+1]+: 342.90.

Aufarbeitung

  1. customTo the resulting reaction mixture
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-79ec7484bf81452ca16b99b667878be6
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088368B2

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