Triethylamine → Benzo[b]thiophen-2-yl(9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 471179

Reaktionsgleichung

Reaktionsgleichung von HRID 471179
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[S:25]1[C:29]([C:30]([OH:32])=O)=[CH:28][C:27]2[CH:33]=[CH:34][CH:35]=[CH:36][C:26]1=2.[Si:37]([O:44][CH2:45][CH2:46][C:47]1[C:48]([F:65])=[C:49]([CH:62]=[CH:63][CH:64]=1)[CH2:50][N:51]1[CH2:61][CH2:60][C:54]2([O:59][CH2:58][CH2:57][NH:56][CH2:55]2)[CH2:53][CH2:52]1)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38].C(N(CC)CC)C>CN(C=O)C>[S:25]1[C:29]([C:30]([N:56]2[CH2:55][C:54]3([CH2:53][CH2:52][N:51]([CH2:50][C:49]4[CH:62]=[CH:63][CH:64]=[C:47]([CH2:46][CH2:45][O:44][Si:37]([C:40]([CH3:42])([CH3:41])[CH3:43])([CH3:38])[CH3:39])[C:48]=4[F:65])[CH2:61][CH2:60]3)[O:59][CH2:58][CH2:57]2)=[O:32])=[CH:28][C:27]2[CH:33]=[CH:34][CH:35]=[CH:36][C:26]1=2

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579891399-(3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecane

Produkt 1

HCID 57989142Benzo[b]thiophen-2-yl(9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.378 g) was added to a stirred solution of benzo[b]thiophene-2-carboxylic acid (0.186 g), 9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecane (example 78, step d) (0.40 g), and triethylamine (0.383 g) in DMF (4 mL). After 1 h, the reaction mixture was partitioned between water and ethyl acetate. The ethyl acetate layer was washed twice with water and once with brine, dried over magnesium sulphate, filtered and evaporated in vacuo. Purification by silica gel chromatography eluting with 7:1:0.5, isohexane:ethyl acetate:triethylamine gave the subtitled compound as a gum. Yield 0.38 g.

Aufarbeitung

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed twice with water and 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 7:1:0.5, isohexane

Quellen und Nachweise

ORD-Eintrag
ord-aedfab2623dd4f54a91c2800eed386d6
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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