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Triethylamine → 2-Methylpentane

HRID 471093
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 471093
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[S:27][C:28]2[CH:34]=[CH:33][C:32]([C:35]([OH:37])=O)=[CH:31][C:29]=2[N:30]=1.[Si:38]([O:45][CH2:46][CH2:47][C:48]1[CH:49]=[C:50]([CH2:53][N:54]2[CH2:64][CH2:63][C:57]3([O:62][CH2:61][CH2:60][NH:59][CH2:58]3)[CH2:56][CH2:55]2)[S:51][CH:52]=1)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39].C(N(CC)CC)C>CN(C=O)C>[CH3:28][CH2:29][CH2:31][CH:32]([CH3:35])[CH3:33].[Si:38]([O:45][CH2:46][CH2:47][C:48]1[CH:49]=[C:50]([CH2:53][N:54]2[CH2:64][CH2:63][C:57]3([O:62][CH2:61][CH2:60][N:59]([C:35]([C:32]4[CH:33]=[CH:34][C:28]5[S:27][C:26]([CH3:25])=[N:30][C:29]=5[CH:31]=4)=[O:37])[CH2:58]3)[CH2:56][CH2:55]2)[S:51][CH:52]=1)([C:41]([CH3:42])([CH3:43])[CH3:44])([CH3:40])[CH3:39]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 6499532-Methyl-1,3-benzothiazole-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579891139-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecane

Produkt 2

HCID 7892
2-Methylpentane
HCID 57989353(9-((4-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylbenzo[d]thiazol-5-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HATU (0.333 g) was added to stirred solution of 2-methylbenzo[d]thiazole-5-carboxylic acid (0.17 g), 9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecane (example 43, step b) (0.3 g) and triethylamine (0.407 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, once with brine, dried over magnesium sulphate, filtered and evaporated in vacuo. Purification by silica gel chromatography eluting with ethyl acetate:isohexane:triethylamine, 2:8:1 gave the subtitled compound as a gum. Yield 0.36 g.

Aufarbeitung

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed twice with water, once with 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-9a8f087a66bc49038e372dd3062a1b28
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08629271B2

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