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Dicyclohexylcarbodiimide → 3(R)-[3-cyclopentanone-1(R)-carboxamido]-4-oxo-2(S)-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide

HRID 345163
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 345163
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11](OCC)=[O:12])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[S:4][C@H:3]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:26]1[CH:31]([C:32]([OH:34])=O)[CH2:30][C:28](=[O:29])[CH2:27]1.O[N:36]1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C@@H:31]1([C:32]([NH:1][C@@H:2]2[C:8](=[O:9])[N:7]([CH2:10][C:11]([NH2:36])=[O:12])[C:6]3[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=3[S:4][C@H:3]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:34])[CH2:26][CH2:27][C:28](=[O:29])[CH2:30]1
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Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2277983-Oxocyclopentanecarboxylic acidHCID 14648534Ethyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

Produkt 1

HCID 679241153(R)-[3-cyclopentanone-1(R)-carboxamido]-4-oxo-2(S)-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 10 ml of dry dimethylformamide of 511 mg of ethyl 3(R)-amino-4-oxo-2(S)-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate, 200 mg of 3-cyclopentanone-1(R)-carboxylic acid which is prepared according to the known procedure and 322 mg of 1-hydroxybenzotriazole is added 322 mg of dicyclohexylcarbodiimide. After allowing to stand overnight, the precipitated dicyclohexylurea is filtered off. The dimethylformamide was distilled off under reduced pressure, and to the residue is added chloroform. After washing with an aqueous solution of sodium chloride and drying over magnesium sulfate, the solvent is distilled off. The residue is subjected to column chromatography on silica gel and crystallized from benzene to give 540 ml of 3(R)-[3-cyclopentanone-1(R)-carboxamido]-4-oxo-2(S)-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide, m.p.=135°- 150° C.

Aufarbeitung

  1. filtrationthe precipitated dicyclohexylurea is filtered off
  2. distillationThe dimethylformamide was distilled off under reduced pressure
  3. additionto the residue is added chloroform
  4. washAfter washing with an aqueous solution of sodium chloride
  5. dry with materialdrying over magnesium sulfate
  6. distillationthe solvent is distilled off
  7. customcrystallized from benzene

Quellen und Nachweise

ORD-Eintrag
ord-dd6ac23e2d124db0b2453634674fe2e4
Quelldatensatz
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05055464

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