1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-3-(4-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoylamino)-2-hydroxy-propionic acid methyl ester

HRID 412458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412458
[C:1]([O:5][C:6]([N:8]([CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:52][O:53][C:54](=[O:59])[C@H:55]([OH:58])[CH2:56][NH2:57]>CN(C=O)C.C(N(C(C)C)CC)(C)C.O>[CH3:52][O:53][C:54](=[O:59])[C@H:55]([OH:58])[CH2:56][NH:57][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([CH2:21][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:9]2[CH:10]=[CH:11][C:12]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[CH:23][CH:24]=1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11665404methyl (2R)-3-amino-2-hydroxypropanoateHCID 223111164-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoic acid

Produkt 1

HCID 69733520(R)-3-(4-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoylamino)-2-hydroxy-propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

4-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoic acid was dissolved in DMF (10 mL) and HOBt (0.40 g, 2.93 mmol) and EDAC (0.52 g, 2.73 mmol) were added. The reaction mixture was stirred for 45 min. Then a solution of (R)-3-amino-2-hydroxypropionic acid methyl ester in DMF (8 mL) and diisopropylethylamine (0.46 mL) were added. The mixture was stirred overnight. The reaction mixture was diluted with water (40 mL) and extracted with ethyl acetate (75 mL). The aqueous phase was extracted with ethyl acetate (30 mL). The combined organic phases were washed with hydrochloric acid (0.2 N, 3×30 mL), water: saturated sodium chloride (3×30 mL), dried with magnesium sulphate and concentrated in vacua. The residue was purified by column chromatography on silica gel (100 g) using mixtures of ethyl acetate and n-heptane (1 L (1:1) and 0.5 L (7:3)) as eluents to afford 0.77 g (R)-3-(4-{[tert-butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoylamino)-2-hydroxypropionic acid methyl ester.

Aufarbeitung

  1. stirringThe mixture was stirred overnight
  2. extractionextracted with ethyl acetate (75 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (30 mL)
  4. washThe combined organic phases were washed with hydrochloric acid (0.2 N, 3×30 mL), water
  5. dry with materialsaturated sodium chloride (3×30 mL), dried with magnesium sulphate
  6. concentrationconcentrated in vacua
  7. customThe residue was purified by column chromatography on silica gel (100 g)

Quellen und Nachweise

ORD-Eintrag
ord-0ded09a6921449428dca448752461c6d
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562807B2

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