1-Hydroxybenzotriazole → (S)-t-Butyl 2-(2-(2-(3,4-dimethoxyphenoxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate

HRID 710039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710039
[NH:1]([C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4])[NH2:2].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[O:22][CH2:23][C:24](O)=[O:25].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[O:22][CH2:23][C:24]([NH:2][NH:1][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4])=[O:25]

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10014050tert-Butyl (2S)-2-(hydrazinecarbonyl)pyrrolidine-1-carboxylateHCID 21835839HCID 21835839, Verbindung

Produkt 1

HCID 86706750(S)-t-Butyl 2-(2-(2-(3,4-dimethoxyphenoxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylateAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of (S)-t-butyl 2-(hydrazinecarbonyl)pyrrolidine-1-carboxylate (50.0 g) and 2-(3,4-dimethoxyphenoxy)acetic acid (47.8 g) in chloroform (1000 ml), HOBt (35.3 g) and WSC hydrochloride (50.0 g) were added and the mixture was stirred at room temperature for 4 hours. After distilling off the solvent under reduced pressure, water was added, followed by extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate and brine and dried over MgSO4 before it was filtered. The solvent was distilled off under reduced pressure to give a crude form of the titled compound (61.0 g).

Aufarbeitung

  1. distillationAfter distilling off the solvent under reduced pressure, water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over MgSO4 before it
  6. filtrationwas filtered
  7. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f0563710e9da4890b82dcb6b60a8fa9f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181229B2

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