2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → tert-butyl 2-(N-(5-bromo-2-methoxybenzyl)-2,2-dimethylchroman-6-sulfonamido)acetate

HRID 1805955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805955
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12]([NH:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(=[O:14])=[O:13])[CH:8]=2)[O:3]1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[Br:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([CH2:52]Br)[CH:45]=1>CC#N>[Br:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([CH:45]=1)[CH2:52][N:15]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:24])([CH3:1])[CH2:11][CH2:10]2)(=[O:14])=[O:13]

Komponenten

5

Edukt 3

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 49627394-Bromo-2-(bromomethyl)-1-methoxybenzeneHCID 58409094Tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate

Produkt 1

HCID 58409099tert-butyl 2-(N-(5-bromo-2-methoxybenzyl)-2,2-dimethylchroman-6-sulfonamido)acetateAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To the solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (500 mg, 1.407 mmol) in MeCN (15 mL) was added resin-supported BEMP (786 mg, 1.547 mmol) and 4-bromo-2-(bromomethyl)-1-methoxybenzene (500 mg, 1.786 mmol). The mixture was heated in a microwave synthesizer at 90° C. for 3 hours. The reaction mixture was filtered, rinsed alternatively by dichloromethane and methanol. The filtrate was concentrated to give a reddish orange residue, which was purified by silica chromatography to obtain a white powder (700 mg, 85% yield). 1H NMR (500 MHz, CDCl3) δ 7.56-7.50 (m, 2H), 7.34-7.29 (m, 2H), 6.81 (d, J=8.1 Hz, 1H), 6.66 (d, J=8.5 Hz, 1H), 4.47 (s, 2H), 3.88 (s, 2H), 3.71 (s, 3H), 2.78 (t, J=6.7 Hz, 2H), 1.82 (t, J=6.7 Hz, 2H), 1.38 (s, 9H), 1.34 (s, 6H). LRMS [ESI, MH−] m/z calcd for C25H33BrNO6S 554.12, found 554.1.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washrinsed alternatively by dichloromethane and methanol
  3. concentrationThe filtrate was concentrated
  4. customto give a reddish orange residue, which
  5. customwas purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d6b3d7a0ec214581b6a5ab24dc207535
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354548B2

Notizen zur Reaktion

Wird geladen…