Potassium Hydroxide → Benzyl 4-{2-[(di-tert-butoxyphosphoryl)oxy]ethyl}-3-oxopiperazine-1-carboxylate

HRID 640025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 640025
[P:1]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])([O:3][CH2:4][CH2:5]Br)=[O:2].[O:17]=[C:18]1[NH:23][CH2:22][CH2:21][N:20]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:19]1.[OH-].[K+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:8]([O:7][P:1]([O:3][CH2:4][CH2:5][N:23]1[CH2:22][CH2:21][N:20]([C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])[CH2:19][C:18]1=[O:17])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:2])([CH3:11])([CH3:10])[CH3:9]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 866093932-Bromoethyl di-tert-butyl phosphate

Produkt 1

HCID 68638741Benzyl 4-{2-[(di-tert-butoxyphosphoryl)oxy]ethyl}-3-oxopiperazine-1-carboxylateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-Bromoethyl di-tert-butyl phosphate (298 mg, 0.94 mmol) in tetrahydrofuran (1.0 ml) was added at room temperature to a stirred suspension of benzyl 3-oxopiperazine-1-carboxylate (200 mg, 0.85 mmol), powdered potassium hydroxide (57 mg, 1.0 mmol) and tetra-n-butylammonium bromide (55 mg, 0.17 mmol) in THF (2.0 ml). The reaction mixture was stirred for 90 minutes and then filtered through Celite and the filtrate evaporated to leave a colourless oil. The crude product was purified by silica gel chromatography eluting with a 2-5% mixture of methanol in dichloromethane to give benzyl 4-{2-[(di-tert-butoxyphosphoryl)oxy]ethyl}-3-oxopiperazine-1-carboxylate (220 mg, 55% yield) as a colourless oil:

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customthe filtrate evaporated
  3. customto leave a colourless oil
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with a 2-5% mixture of methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-fe11192f03fa40568e15dcbb61c189b1
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691867B2

Notizen zur Reaktion

Wird geladen…