Triethylamine → 2-Methylpentane

HRID 1689208

Reaktionsgleichung

Reaktionsgleichung von HRID 1689208
CCCP1(OP(CCC)(=O)OP([CH2:16][CH2:17][CH3:18])(=O)O1)=O.Cl.[O:20]1[C:25]2([CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)[CH2:24][NH:23][CH2:22][CH2:21]1.[CH3:38][C:39]1[S:43][C:42]([C:44](O)=[O:45])=[CH:41][CH:40]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH3:24][CH2:25][CH2:26][CH:17]([CH3:16])[CH3:18].[CH3:38][C:39]1[S:43][C:42]([C:44]([N:23]2[CH2:24][C:25]3([CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)[O:20][CH2:21][CH2:22]2)=[O:45])=[CH:41][CH:40]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 747135-Methylthiophene-2-carboxylic acidHCID 111923Propylphosphonic anhydrideHCID 66964240Tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride

Produkt 2

HCID 78922-MethylpentaneHCID 57989101Tert-butyl 4-(5-methylthiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Propanephosphonic acid cyclic anhydride (1.57M solution in THF, 0.64 mL) was added to a solution of tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (WuXi PharmaTech) (0.26 g), 5-methylthiophene-2-carboxylic acid (0.142 g) and triethylamine (0.84 mL) in DMF (8 mL) and the resulting mixture stirred for 16 h. The reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (3×200 mL). The combined organic solutions were washed with water (2×100 mL) and brine (100 mL), then dried over magnesium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with ethyl acetate:isohexane, 1:1 to give the subtitled compound as a clear oil. Yield 0.32 g.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. washThe combined organic solutions were washed with water (2×100 mL) and brine (100 mL)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification
  7. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2bea720a39d74bf59b258f8b62f8270c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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