Dimethylformamide → 3-{4-[1-(4-Tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

HRID 412441

Reaktionsgleichung

Reaktionsgleichung von HRID 412441
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:27]2[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=2C(O)=O)[NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ON1C2N=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.[CH2:58]([O:60][C:61](=[O:66])[CH:62]([OH:65])[CH2:63][NH2:64])[CH3:59].C(N(C(C)C)CC)(C)C.CN([CH:79]=[O:80])C>C(Cl)Cl>[CH2:58]([O:60][C:61](=[O:66])[CH:62]([OH:65])[CH2:63][NH:64][C:79](=[O:80])[C:33]1[CH:32]=[CH:28][C:27]([CH:11]([NH:12][C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:20][CH:21]=2)=[O:14])[C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:6][CH:7]=2)=[CH:35][CH:34]=1)[CH3:59]

Komponenten

8

Edukt 6

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 22311167[1-(4-Tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoic acidHCID 85611992(RS)-isoserine ethyl ester hydrochloride

Produkt 1

HCID 674831433-{4-[1-(4-Tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of [1-(4-tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoic acid (1.0 g, 2.06 mmol) in DMF (1 mL) and DCM (10 mL) was added 1-hydroxy-7-azabenzo-triazole (0.33 g, 2.47 mmol). After stirring for 1 hour at room temperature, EDAC (0.47 g, 2.47 mmol), (RS)-isoserine ethyl ester hydrochloride (0.52 g, 3.09 mmol) and diisopropylethylamine (1.1 mL, 6.18 mmol) were added, successively. After stirring for 17 hours at ambient temperature the reaction mixture was partitioned between water, brine and ethyl acetate. The aqueous phase was further extracted with ethyl acetate. The combined organic phases were washed with water and brine. After drying (magnesium sulphate) and filtration, the organic phase was evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (6:4). This afforded 1.2 g (97%) of (RS)-3-{4-[1-(4-tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]-benzoylamino}-2-hydroxypropionic acid ethyl ester as an oil.

Aufarbeitung

  1. stirringAfter stirring for 17 hours at ambient temperature the reaction mixture
  2. customwas partitioned between water, brine and ethyl acetate
  3. extractionThe aqueous phase was further extracted with ethyl acetate
  4. washThe combined organic phases were washed with water and brine
  5. customAfter drying
  6. filtration(magnesium sulphate) and filtration
  7. customthe organic phase was evaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (6:4)

Quellen und Nachweise

ORD-Eintrag
ord-d53d1a0d06444e1d99af7a08a9c1ce3b
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562807B2

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