Diethylamine → HCID 10503756, Verbindung

HRID 353438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353438
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:24])[C:15]2[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(Cl)=O)C(C)C.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:24])[C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:22])[N:35]([CH2:36][CH3:37])[CH2:33][CH3:34])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 8021DiethylamineHCID 62365Isobutyl chloroformateHCID 10834544HCID 10834544, Verbindung

Produkt 1

HCID 10503756HCID 10503756, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of compound 5 (1.0 g, 2.5 mmol) in dry dichloromethane (10 mL) at −20° C. was added isobutylchloroformate (450 mg, 3.3 mmol). After 20 min at −20° C. diethylamine (4 mL) was added and the reaction was allowed to warm to room temperature. After 1.5 hrs the solvents were evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4. Removal of solvents provided a crude product, which was purified by flash chromatography to give compound 6 as white needles (800 mg, 73%): IR (NaCl) 3051, 2975, 1694, 1633, 1416, 1281, 1168, 1115 cm−1; 1H NMR (CDCl3) δ1.13 (br, 3H), 1.22 (br, 3H), 1.44 (s, 9H),2.22 (t, J=5.5 Hz, 2H), 2.62 (t, J=5.5 Hz, 2H), 3.33 (m, 4H), 3.55 (m, 2H), 7.31 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H); 13C NMR (CDCl3) δ12.71, 14.13, 28.3, 31.5, 34.2, 39.1, 43.2, 79.7, 115.9, 126.3, 129.3, 136.8, 137.1, 140.6, 154.6, 170.

Aufarbeitung

  1. customAfter 1.5 hrs the solvents were evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. customRemoval of solvents
  6. customprovided a crude product, which
  7. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6557d14af52344c5bbc22dc4abf27f52
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06753335B2

Notizen zur Reaktion

Wird geladen…