tert-Butanol → N-(t-butoxycarbonylsulfamoyl)-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester

HRID 643952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643952
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[CH3:13][O:14][C:15](=[O:39])[CH2:16][NH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:24][C:23](=[O:36])[C:22]([O:37][CH3:38])=[CH:21]2.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:13][O:14][C:15](=[O:39])[CH2:16][N:17]([S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:24][C:23](=[O:36])[C:22]([O:37][CH3:38])=[CH:21]2

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 86624027(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-ylamino)-acetic acid methyl ester

Produkt 1

HCID 86624028N-(t-butoxycarbonylsulfamoyl)-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of chlorosulfonyl isocyanate (0.15 mL, 1.75 mmol) in 4 mL of CH2Cl2, cooled in a ice bath, is added t-butanol (0.17 mL, 1.75 mmol). The mixture is warmed to ambient temperature and stirred for 15 min. The solution is cooled in an ice bath and a solution of (7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-ylamino)-acetic acid methyl ester (0.430 g, 1.17 mmol) and triethylamine (0.35 mL, 2 mmol) is added dropwise. After addition is complete, the mixture is warmed to ambient temperature and stirred for 1.5 h. To this is added water (1 mL) and the mixture is extracted with EtOAc. The organic layer is washed with water, sat. NaCl and dried over sodium sulfate. The solvent is removed under reduced pressure to afford N-(t-butoxycarbonylsulfamoyl)-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester as a white solid: 1H NMR (CDCl3) δ 7.78 (s, 1H), 7.71 (s, 1H), 7.38-7.30 (m, 5H), 6.82, (s, 1H), 6.78 (s, 1H), 5.18 (s, 2H), 4.55 (s, 2H), 3.83 (s, 3H); 3.66 (s, 3H), 1.41 (s, 9H); (M+H)+=549.

Aufarbeitung

  1. temperatureThe solution is cooled in an ice bath
  2. additionAfter addition
  3. temperaturethe mixture is warmed to ambient temperature
  4. stirringstirred for 1.5 h
  5. extractionthe mixture is extracted with EtOAc
  6. washThe organic layer is washed with water, sat. NaCl
  7. dry with materialdried over sodium sulfate
  8. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4e44a4ef47af4328acf9f1487114ace3
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700633B2

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