1-Hydroxybenzotriazole → tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-({[(1-methylethoxy)acetyl]amino}methyl)-1,4-oxazepane-4-carboxylate

HRID 1022630

Reaktionsgleichung

Reaktionsgleichung von HRID 1022630
[NH2:1][CH2:2][C@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([F:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1.[CH3:25][CH:26]([O:28][CH2:29][C:30](O)=[O:31])[CH3:27].N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C1COCC1.C(N(CC)CC)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C@@H:9]2[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4][C@H:3]2[CH2:2][NH:1][C:30](=[O:31])[CH2:29][O:28][CH:26]([CH3:27])[CH3:25])=[CH:11][C:12]=1[F:17]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 5172132-(Propan-2-yloxy)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66975002tert-butyl (6R,7R)-6-(aminomethyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate

Produkt 1

HCID 66975815tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-({[(1-methylethoxy)acetyl]amino}methyl)-1,4-oxazepane-4-carboxylateAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (6R,7R)-6-(aminomethyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate (300 mg), (1-methylethoxy)acetic acid (119 mg), 1H-benzotriazol-1-ol (136 mg) and triethylamine (0.291 ml) in THF (4.2 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (192 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added distilled water, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (384 mg).

Aufarbeitung

  1. additionTo the reaction mixture was added
  2. distillationdistilled water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with distilled water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e983728b8b4e4c029f430f4452e2c52d
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722662B2

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