1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-3-{4-[1-(4-cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

HRID 967628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 967628
C1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([O:37][CH3:38])[CH:28]=2)=[O:25])[C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)CCCCC1.[CH:39]1[CH:40]=[CH:41][C:42]2N(O)N=N[C:43]=2[CH:44]=1.CCN=C=NCCCN(C)C.[CH2:60]([O:62][C:63](=[O:68])[C@H:64]([OH:67])[CH2:65][NH2:66])[CH3:61]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:60]([O:62][C:63](=[O:68])[C@H:64]([OH:67])[CH2:65][NH:66][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([CH:13]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=[C:29]([O:37][CH3:38])[CH:28]=2)=[O:25])[C:8]2[CH:9]=[CH:10][C:11]([CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]3)=[CH:12][CH:7]=2)=[CH:15][CH:16]=1)[CH3:61]

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 223111384-[1-(Cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoic acidHCID 54263093ethyl (2R)-3-amino-2-hydroxypropanoate

Produkt 1

HCID 67483036(R)-3-{4-[1-(4-cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl esterAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-[1-(Cyclohexylphenyl)-3-(3-methoxy-5-trifluormethylphenyl)ureidomethyl]benzoic acid (420 mg, 0.8 mmol) was dissolved in DMF (10 mL), and then HOBt (160 mg, 1.2 mmol) and EDAC (230 mg, 1.2 mmol) were added. The reaction mixture was allowed to stand for 30 min, then (R)-isoserine ethyl ester (260 mg, 1.2 mmol) and dissopropylethylamine (210 mL, 1.2 mmol) dissolved in DMF (5 mL) were added and the reaction mixture was stirred at room temperature for 16 hours. Water (50 mL) and ethyl acetate (100 mL) were added and the organic phase was washed with water (5×50 mL), dried (magnesium sulphate), filtered and evaporated in vacuo. The residue was purified by column chromatography on silica gel, eluting with a mixture of heptane and ethyl acetate (1:3) to afford 510 mg of (R)-3-{4-[1-(4-cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester as an amorphous solid.

Aufarbeitung

  1. additionwere added
  2. washthe organic phase was washed with water (5×50 mL)
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of heptane and ethyl acetate (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-5828315428a943eb9238a822a9c4c7bf
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953812B2

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