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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (10S)-2-acetylthiomethyl-4-methyl-N-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide

HRID 849730
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Reaktionsgleichung

Reaktionsgleichung von HRID 849730
[CH3:1][CH:2]([CH3:13])[CH2:3][CH:4]([CH2:8][S:9][C:10](=[O:12])[CH3:11])[C:5]([OH:7])=O.[O:14]=[C:15]1[CH2:32][CH2:31][C:30]2=[CH:33][N:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=32)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][NH:16]1.CC[N:36]=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[C:10]([S:9][CH2:8][CH:4]([CH2:3][CH:2]([CH3:1])[CH3:13])[C:5]([NH:36][C@H:32]1[CH2:31][C:30]2=[CH:33][N:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=32)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][NH:16][C:15]1=[O:14])=[O:7])(=[O:12])[CH3:11]
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Komponenten

6

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 130175572-[(Acetylthio)methyl]-4-methylpentanoic acidHCID 700960479-Oxo-1,8-diaza-tricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraene

Produkt 1

HCID 86752869(10S)-2-acetylthiomethyl-4-methyl-N-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-methyl-2-acetylthiomethylpentanoic acid (612 mg, 3 mmol), (10S)-10-amino-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraene (427 mg, 1.5 mmol), and HOBtH2O (230 mg, 1.5 mmol) in dry DMF (30 mL) under argon at room temperature was added EDCI (863 mg, 4.5 mmol) in one portion. After stirring overnight, DMF was removed at 30° C. under high vacuum to give a yellowish semi-solid. It was dissolved in ethyl acetate (50 mL), washed with 1N HCl (30 mL), 5% NaHCO3 solution (30 mL) and finally brine (30 mL). The organic layer was dried (MgSO4) and evaporated to dryness. The resulting pale yellow-oil was stirred in 50% ether-pet. ether (40 mL) to yield 600 mg (85%) of (10S)-2-acetylthiomethyl-4-methyl-N-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide as 1:1 stereoisomeric mixture. The stereoisomeric mixture was separated in flash column chromatography (LPS-2), eluted with 20% ethyl acetate in pet. ether to give the less polar stereoisomer, m.p. 226° C., and the more polar stereoisomer, m.p. 220° C.

Aufarbeitung

  1. customDMF was removed at 30° C. under high vacuum
  2. customto give a yellowish semi-solid
  3. washwashed with 1N HCl (30 mL), 5% NaHCO3 solution (30 mL) and finally brine (30 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated to dryness
  6. stirringThe resulting pale yellow-oil was stirred in 50% ether-pet. ether (40 mL)

Quellen und Nachweise

ORD-Eintrag
ord-9d2effa9f6c547cca0aa6fa4ed295f68
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06013792

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