Triethylamine → tert-Butyl 4-(2-isopropylthiazole-5-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

HRID 1689495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689495
Cl.[O:2]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH:27]([C:30]1[S:31][C:32]([C:35](O)=[O:36])=[CH:33][N:34]=1)([CH3:29])[CH3:28].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C>[CH:27]([C:30]1[S:31][C:32]([C:35]([N:5]2[CH2:6][C:7]3([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]3)[O:2][CH2:3][CH2:4]2)=[O:36])=[CH:33][N:34]=1)([CH3:29])[CH3:28]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 197863422-(Propan-2-yl)-1,3-thiazole-5-carboxylic acidHCID 66964240Tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride

Produkt 1

HCID 57989386tert-Butyl 4-(2-isopropylthiazole-5-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (WuXi PharmaTech) (0.694 g) in DMF (13 mL) was treated with triethylamine (1.3 mL), followed by 2-isopropylthiazole-5-carboxylic acid (example 55, step b) (0.406 g) and then O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.26 g). The resulting mixture was stirred at RT for 16 h. DMF was removed in vacuo. The residue was taken up in EtOAc (40 mL) and washed with saturated sodium bicarbonate solution (2×40 mL), water (40 mL) and brine (40 mL), dried over sodium sulphate, filtered and evaporated in vacuo. The viscous orange oil was purified by silica gel chromatography eluting with 0-7% MeOH in DCM to give the subtitled compound as a viscous orange oil. Yield 0.765 g.

Aufarbeitung

  1. customDMF was removed in vacuo
  2. washwashed with saturated sodium bicarbonate solution (2×40 mL), water (40 mL) and brine (40 mL)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe viscous orange oil was purified by silica gel chromatography
  7. washeluting with 0-7% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-654c166086564a639365eabb198fb90c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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