tert-Butanol → 4-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid tert-butyl ester

HRID 661638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661638
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[C:5]([N:7]([CH3:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:6].C(Cl)(=O)C(Cl)=O.[C:31](O)([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl>[C:31]([O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:7]([C:5](=[O:6])[C:4]1[CH:21]=[CH:22][C:23]([Cl:24])=[C:2]([Br:1])[CH:3]=1)[CH3:20])([CH3:34])([CH3:33])[CH3:32]

Komponenten

5

Edukt 3

HCID 6386tert-ButanolHCID 65578Oxalyl chlorideHCID 686025894-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid

Produkt 1

HCID 686027474-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid tert-butyl esterAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a cooled solution (0° C.) of 4-{2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid (1.07 g, 2.60 mmol) in anhydrous DCM (10 mL), oxalyl chloride (0.34 mL, 3.90 mmol) was added dropwise. The mixture was stirred at room temperature for 4 hours, concentrated in vacuo and redissolved in anhydrous dichloromethane (5 mL). A solution of t-butanol (960 mg, 13 mmol) in anhydrous DCM (5 mL) was added and the mixture was stirred at room temperature overnight. After dilution with DCM, the mixture was washed with sat NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. Purification by silica gel column chromatography (EtOAc/Hexanes: 1/4 with gradient up to EtOAc/Hexanes 1/3) afforded 1.1 g of 4-{2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid tert-butyl ester as a colorless oil. MS [M+H]+ (fragment): 411.7 (f; tR=3.10 min, (method 1)

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionredissolved in anhydrous dichloromethane (5 mL)
  3. stirringthe mixture was stirred at room temperature overnight
  4. washAfter dilution with DCM, the mixture was washed with sat NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel column chromatography (EtOAc/Hexanes: 1/4 with gradient up to EtOAc/Hexanes 1/3)

Quellen und Nachweise

ORD-Eintrag
ord-ab91079ea11545328a4b69fcd89e9dd6
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084614B2

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