1,2-Dichloroethane → HCID 178451952, Verbindung

HRID 1401122

Reaktionsgleichung

Reaktionsgleichung von HRID 1401122
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[S:16]1[C:20]([NH2:21])=[CH:19][N:18]=[N:17]1.C(Cl)CCl.[CH:26]1[CH:27]=[CH:28][C:29]2N(O)N=N[C:30]=2[CH:31]=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([SH:16]1[C:20]([NH2:21])=[C:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:18]=[N:17]1)=[O:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Komponenten

9

Edukt 6

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 777361,2,3-Thiadiazol-5-amineHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 516892Sodium Bicarbonate

Produkt 1

HCID 178451952HCID 178451952, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Boc-L-Proline (9.7 g, 45.2 mmol), 4-phenyl-1,2,3,-thiadiazol-5-amine (4.0 g, 22.6 mmol), EDC (8.2 g, 42.9 mmol), HOBt (5.8 g, 42.9 mmol), DIPEA (19.7 ml, 113 mmol) were combined and stirred for 3 days in 40 ml DMF at 60 deg C. Ethyl acetate and saturated aqueous NaHCO3 were added. The aqueous layer was separated and extracted with ethyl acetate. Organic layers were combined and washed with aqueous NaHCO3 and brine. Organic layer was dried over MgSO4 and concentrated to a brown residue. Pure Boc-prolyl-4-phenyl-5-amino-1,2,3-thiadiazole c was obtained by crystallization from 100 ml hot acetonitrile to obtain 5.9 g. Calculated mass 374.5. found 375.3.

Aufarbeitung

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate
  3. washwashed with aqueous NaHCO3 and brine
  4. dry with materialOrganic layer was dried over MgSO4
  5. concentrationconcentrated to a brown residue

Quellen und Nachweise

ORD-Eintrag
ord-92430ae85e3449c381d63675680a8fa8
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907092B2

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