Triethylamine → 2-Methylpentane

HRID 471071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471071
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([C:29]1[S:30][CH:31]=[C:32]([C:34]([OH:36])=O)[N:33]=1)([CH3:28])([CH3:27])[CH3:26].[Si:37]([O:44][CH2:45][CH2:46][C:47]1[CH:48]=[C:49]([CH2:52][N:53]2[CH2:63][CH2:62][C:56]3([O:61][CH2:60][CH2:59][NH:58][CH2:57]3)[CH2:55][CH2:54]2)[S:50][CH:51]=1)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38].C(N(CC)CC)C>CN(C=O)C>[CH3:52][CH2:49][CH2:48][CH:47]([CH3:51])[CH3:46].[Si:37]([O:44][CH2:45][CH2:46][C:47]1[CH:48]=[C:49]([CH2:52][N:53]2[CH2:63][CH2:62][C:56]3([O:61][CH2:60][CH2:59][N:58]([C:34]([C:32]4[N:33]=[C:29]([C:25]([CH3:26])([CH3:27])[CH3:28])[S:30][CH:31]=4)=[O:36])[CH2:57]3)[CH2:55][CH2:54]2)[S:50][CH:51]=1)([C:40]([CH3:41])([CH3:42])[CH3:43])([CH3:39])[CH3:38]

Komponenten

7

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 288755552-Tert-butyl-1,3-thiazole-4-carboxylic acidHCID 579891139-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecane

Produkt 2

HCID 78922-MethylpentaneHCID 57989351(9-((4-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-tert-butylthiazol-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HATU (0.306 g) was added to stirred solution of 2-tert-butylthiazole-4-carboxylic acid (0.16 g), 9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecane (example 43, step b) (0.300 g) and triethylamine (0.41 mL) in DMF (3 mL). After 1 h, the reaction mixture was partitioned between water and ethyl acetate. The ethyl acetate layer was washed twice with water and brine, dried over magnesium sulphate, filtered and evaporated in vacuo. Purification by silica gel chromatography eluting with ethyl acetate:isohexane:triethylamine, 12:90:10 gave the subtitled compound as a gum. Yield 0.3 g.

Aufarbeitung

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed twice with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by silica gel chromatography
  7. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5ee7b2a08ed94c7682043301594e4b1b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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