tert-butyl (E)-(2S,3S)-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-3-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidine-3-carbonyl)-2-(2-methoxy-ethyl)-undec-4-enoate → tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-11-(2-hept yl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate

HRID 1779197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1779197
[CH2:1]([C:8]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]/[CH:19]=[CH:20]/[C@H:21]([C:35](N2[C@@H](C(C)C)C(C3C=CC=CC=3)(C3C=CC=CC=3)OC2=S)=[O:36])[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[O:12][CH2:11][CH2:10][O:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[NH2:58][C@@H:59]([CH2:64][C:65]1[CH:70]=[CH:69][C:68]([O:71][CH2:72][CH2:73][CH2:74][CH3:75])=[CH:67][CH:66]=1)[C:60]([NH:62][CH3:63])=[O:61]>ClCCl>[CH2:72]([O:71][C:68]1[CH:67]=[CH:66][C:65]([CH2:64][C@H:59]([NH:58][C:35]([C@@H:21](/[CH:20]=[CH:19]/[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:8]2([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[O:9][CH2:10][CH2:11][O:12]2)[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:36])[C:60](=[O:61])[NH:62][CH3:63])=[CH:70][CH:69]=1)[CH2:73][CH2:74][CH3:75]

Komponenten

4

Edukt 2

HCID 90060091tert-butyl (E)-(2S,3S)-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-3-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidine-3-carbonyl)-2-(2-methoxy-ethyl)-undec-4-enoateHCID 90060342(S)-2-amino-3-(4-butoxy-phenyl)-N-methyl-propionamide

Produkt 1

HCID 131734861tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-11-(2-hept yl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

No. 6801291, tert-butyl (E)-(2S,3S)-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-3-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidine-3-carbonyl)-2-(2-methoxy-ethyl)-undec-4-enoate (62 mg, 0.0824 mmol) and (S)-2-amino-3-(4-butoxy-phenyl)-N-methyl-propionamide (23 mg, 0.0989 mmol) were dissolved in dichloromethane. The solvent was distilled off under reduced pressure. The resulting residue was reacted at 45° C. for 4 days. After confirming the consumption of the starting materials by LCMS, the reaction mixture was purified with SP1 to obtain No. 6801292, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-11-(2-hept yl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate (33 mg, 54% yield, ESI (LC/MS positive mode) m/z 762 (M+H); Rt 3.02 min.). To the obtained No. 6801292 (40 mg, 0.0526 mmol) were added dichloromethane (3.0 mL) and trifluoroacetic acid (1.0 mL), and the mixture was stirred at room temperature. After confirming the consumption of the starting materials by LCMS, the solvent was distilled off under reduced pressure. The residue was purified by preparative HPLC. The purified fraction was freeze-dried to obtain the title compound (27 mg, 78% yield, white powder).

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure
  2. customThe resulting residue was reacted at 45° C. for 4 days
  3. customthe consumption of the starting materials by LCMS
  4. customthe reaction mixture was purified with SP1
  5. customto obtain No

Quellen und Nachweise

ORD-Eintrag
ord-746b45a9c53d498eb57d674b2f6090d4
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266853B2

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