1,2-Dichloroethane → HCID 69656109, Verbindung

HRID 857787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857787
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[C:14]([Cl:15])=[N:13][S:12][N:11]=2)=[C:6]([CH2:8][NH2:9])[CH:7]=1.[C:16]([O:20][C:21]([NH:23][C@H:24]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:25]([N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29](O)=[O:30])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:16]([O:20][C:21]([NH:23][C@H:24]([CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1)[C:25]([N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([NH:9][CH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[C:10]1[C:14]([Cl:15])=[N:13][S:12][N:11]=1)=[O:30])=[O:26])=[O:22])([CH3:19])([CH3:17])[CH3:18]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 99754321-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-prolineHCID 21866225HCID 21866225, Verbindung

Produkt 1

HCID 69656109HCID 69656109, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-[5-chloro-2-(4-chloro-1,2,5-thiadiazol-3-yl)phenyl]methanamine (28.1 mg, 0.11 mmol), 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline (prepared by standard peptide coupling protocols, 38.3 mg, 0.11 mmol) and HOAt (19.1 mg, 0.14 mmol) in DMF (1.0 mL) was added EDC (26.9 g, 0.14 mmol). After 16 h the mixture was partitioned between EtOAc and water. The organic phase was washed with brine dried (Na2SO4) and reduced in vacuo. The residue was purified by HPLC (C18 eluting with an acetonitrile/water/0.1% TFA gradient). 1-{(2R)-2-[(tert-Butoxycarbonyl)amino]-2-cyclohexylethanoyl}-N-[5-chloro-2-(4-chloro-1,2,5-thiadiazol-3-yl)benzyl]-L-prolinamide was obtained as a solid. LCMS m/z=596.5.

Aufarbeitung

  1. customAfter 16 h the mixture was partitioned between EtOAc and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customThe residue was purified by HPLC (C18
  5. washeluting with an acetonitrile/water/0.1% TFA gradient)

Quellen und Nachweise

ORD-Eintrag
ord-4ca4d32726054b61bd427dd2aeaae25c
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144899B2

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