Dichloroacetic Acid → HCID 11796530, Verbindung

HRID 2393803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393803
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15]([NH:17][C@@H:18]([CH:39]([CH3:41])[CH3:40])[C:19]([N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]([NH:28][CH:29]([CH:33]([OH:38])[C:34]([F:37])([F:36])[F:35])[CH:30]([CH3:32])[CH3:31])=[O:27])=[O:20])=[O:16].ClC(Cl)C(O)=O.C(OCC)(=O)C>CS(C)=O.C1(C)C=CC=CC=1>[CH3:13][O:14][C:15]([NH:17][C@@H:18]([CH:39]([CH3:41])[CH3:40])[C:19]([N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]([NH:28][CH:29]([C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])[CH:30]([CH3:32])[CH3:31])=[O:27])=[O:20])=[O:16]

Komponenten

7

Edukt 4

HCID 6597Dichloroacetic AcidHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10693669(S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoro-1-hydroxyethyl)propyl]-pyrrolidine-2-carboxamide

Produkt 1

HCID 11796530HCID 11796530, VerbindungAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.84 g) was added to a solution of (S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoro-1-hydroxyethyl)propyl]pyrrolidine-2-carboxamide (0.41 g) dissolved in dimethylsulphoxide (DMSO; 5 ml) and toluene (5 ml), followed by dropwise addition of dichloroacetic acid (0.32 ml). The resulting solution was allowed to stir at 20° C. for 2 hours. The solution was then poured into ethyl acetate (200 ml) and washed successively with 1M hydrochloric acid, water and brine. The organic solution was dried (MgSO4) and concentrated under vacuum. The residue was purified by flash chromatography (gradient elution; methanol:methylene chloride, 3:97 to 5:95) to give (S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoroacetyl)propyl]pyrrolidine-2-carboxamide (0.27 g) as a white foam (as a mixture of ketone and hydrated forms); TLC, Rf =0.4 (methanol:dichloromethane, 2.5:97.5); 1H NMR (DMSO/D2O): 4.44 (m, 1H), 4.00 (m, 2H), 3.72 (m, 1H), 3.51 (m, 4H), 202-1.75 (m, 6H), 0.95-0.78 (m, 12H); Analysis for C18H28F3N3O5 0.3H2O: Calculated: C, 50.42; H, 6.72; N, 9.80; Found: C, 50.31; H, 6.28; N, 9.56.

Aufarbeitung

  1. washwashed successively with 1M hydrochloric acid, water and brine
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography (gradient elution; methanol:methylene chloride, 3:97 to 5:95)

Quellen und Nachweise

ORD-Eintrag
ord-ee7fde0efb004805a3e99d4e136fcdd1
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05808097

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