18-Crown-6 → (+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-3-methoxy-3-oxopropyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174117
CC(C)([O-])C.[K+].[C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17][C:18]3[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[N:14][C:13]=2[CH:37]=1)#[N:8].C1OCCOCCOCCOCCOCCOC1.Br[CH2:57][C:58]([O:60][CH3:61])=[O:59]>C1COCC1>[C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]([C:18]3[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:57][C:58]([O:60][CH3:61])=[O:59])=[N:14][C:13]=2[CH:37]=1)#[N:8]

Komponenten

6

Edukt 4

HCID 2855718-Crown-6HCID 60984Methyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 86701743tert-Butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Produkt 1

HCID 86701760(+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-3-methoxy-3-oxopropyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel4×

Versuchsvorschrift

To a mixture of potassium tert-butoxide (108 mg, 0.958 mmol) in THF (0.715 mL) at −78° C. under nitrogen was added tert-butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 144-A) (200 mg, 0.479 mmol) in THF (4.3 mL) under nitrogen. After stirring for 15 min a solution of 18-crown-6 (12.66 mg, 0.048 mmol) in THF (1.430 mL) was added to the mixture at the same temperature and stirred for another 15 min. Then a solution of methyl bromoacetate (0.618 mL, 6.71 mmol) in THF (0.715 mL) was degassed and added dropwise and stirred at the same temp for 10 min. The reaction mixture was quenched with a saturated solution of ammonium chloride, extracted with EtOAc (2×), passed through a phase separator and concentrated to give the title compound. MS (ESI+) m/z 490.32 (M+H).

Aufarbeitung

  1. additionwas added to the mixture at the same temperature
  2. additionadded dropwise
  3. stirringstirred at the same temp for 10 min
  4. customThe reaction mixture was quenched with a saturated solution of ammonium chloride
  5. extractionextracted with EtOAc (2×)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-19d17045b65f4b0f9efc60df25395c25
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

Notizen zur Reaktion

Wird geladen…