Pyridine → 3-Benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethoxy-ethylsulfamoyl)-benzoic acid methyl ester

HRID 1814357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814357
[C:1]([O:5][C:6](=[O:17])[CH2:7][C@H:8]([NH2:16])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[C:29]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:28]=1>C(Cl)Cl>[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[CH:31][C:30]([S:33](=[O:35])(=[O:34])[NH:16][CH:8]([CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:17])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[C:29]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:28]=1

Komponenten

5

Edukt 3

HCID 1049Pyridine2×HCID 865882243-Benzyloxy-4-chlorosulfonyl-benzoic acid methyl esterHCID 86588238(S)-3-amino-4,4-diethoxy-butyric acid tert-butyl ester

Produkt 1

HCID 697315433-Benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethoxy-ethylsulfamoyl)-benzoic acid methyl esterAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-3-amino-4,4-diethoxy-butyric acid tert-butyl ester (3.38 g, 13.7 mmol) in anhydrous methylene chloride (130 mL) was added pyridine (3.3 mL, 41 mmol) followed by 3-benzyloxy-4-chlorosulfonyl-benzoic acid methyl ester (4.66 g, 13.7 mmol). The reaction was allowed to stir at room temperature overnight. Mass spectrometry and TLC analysis showed presence of starting material. An additional 2 equivalents of pyridine (2.2 mL, 27.3 mmol) was added and allowed to stir overnight. TLC analysis showed the reaction to be completed. The methylene chloride was evaporated and the reaction mixture was dissolved in ether and 5% aqueous citric acid. The organic layer was collected and washed with 5% citric acid and then brine, dried over magnesium sulfate, filtered, and concentrated to yield 3-benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethoxy-ethylsulfamoyl)-benzoic acid methyl ester (6.82 g, 12.4 mmol, 90%) as an orange tar. MS (APCI) m/z 550.3 (M−1).

Aufarbeitung

  1. stirringto stir overnight
  2. customthe reaction
  3. customThe methylene chloride was evaporated
  4. dissolutionthe reaction mixture was dissolved in ether
  5. customThe organic layer was collected
  6. washwashed with 5% citric acid
  7. dry with materialbrine, dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-70e1ba7854fd488b89ea8d30c71d2ce3
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875765B2

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