Triethylamine → HCID 57989088, Verbindung

HRID 470949

Reaktionsgleichung

Reaktionsgleichung von HRID 470949
CCCP1(OP(CCC)(=O)OP(CCC)(=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:40][CH:41]=[C:42]([C:44](O)=[O:45])[N:43]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH3:38][C:39]1[S:40][CH:41]=[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])[N:43]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 2847282-Methyl-1,3-thiazole-4-carboxylic acidHCID 66964240Tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride

Produkt 1

HCID 57989088HCID 57989088, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Propanephosphonic acid cyclic anhydride (1.57M solution in THF, 4.18 mL) was added to a solution of tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (WuXi PharmaTech) (1.92 g), 2-methylthiazole-4-carboxylic acid (0.94 g) and triethylamine (5.48 mL) in DMF (70 mL) and the resulting mixture stirred for 16 h. The reaction mixture was poured into water (500 mL) and extracted with ethyl acetate (3×200 mL). The combined organic solutions were washed with water (2×100 mL) and brine (100 mL), dried over magnesium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with ethyl acetate to give the subtitled compound as a clear oil. Yield 2.30 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-d525b5b5c80547ebbe3364bb93889467
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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