1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl (6SR,7SR)-6-(3,4-dichlorophenyl)-7-{[(1H-1,2,4-triazol-1-ylacetyl)amino]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022814

Reaktionsgleichung

Reaktionsgleichung von HRID 1022814
[NH2:1][CH2:2][CH:3]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][CH:4]1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:46]1([CH2:51][C:52](O)=[O:53])[CH:50]=[N:49][CH:48]=[N:47]1.C(=O)([O-])O.[Na+]>CN(C=O)C.C(N(CC)CC)C>[Cl:24][C:19]1[CH:18]=[C:17]([CH:4]2[CH:3]([CH2:2][NH:1][C:52](=[O:53])[CH2:51][N:46]3[CH:50]=[N:49][CH:48]=[N:47]3)[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]2)[CH:22]=[CH:21][C:20]=1[Cl:23]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 18101801,2,4-Triazole-1-acetic acidHCID 66975190tert-butyl (6RS,7SR)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Produkt 1

HCID 66976357tert-butyl (6SR,7SR)-6-(3,4-dichlorophenyl)-7-{[(1H-1,2,4-triazol-1-ylacetyl)amino]methyl}-1,4-oxazepane-4-carboxylateAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (6SR,7SR)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (200 mg) in DMF (5 mL) were added WSC (100 mg), HOBt (90 mg), triethylamine (0.10 mL) and 2-(1H-1,2,4-triazol-1-yl)acetic acid (74 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (190 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1f6867cb3bf64e0ea833723f471d5ac2
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722662B2

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