Water → (cis)-1-benzoyl-4-tosyloxy-L-proline

HRID 1165971

Reaktionsgleichung

Reaktionsgleichung von HRID 1165971
[C:1]([N:9]1[CH2:17][C@@H:16]([O:18][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:15][C@H:10]1[C:11]([O:13]C)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[OH-].[Li+]>C1COCC1>[C:1]([N:9]1[CH2:17][C@@H:16]([O:18][S:19]([C:22]2[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=2)(=[O:20])=[O:21])[CH2:15][C@H:10]1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 14750327(cis)-1-Benzoyl-4-tosyloxy-L-proline, methyl ester

Produkt 1

HCID 53847232(cis)-1-benzoyl-4-tosyloxy-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (cis)-1-benzoyl-4-tosyloxy-L-proline, methyl ester (from the previous step) in THF.H2O (25 ml-5 ml) was stirred under argon and treated with lithium hydroxide mono hydrate (672 mg, 16 mmole). The reaction was stirred for 3 hours, concentrated in vacuo, acidified to pH 1.5 with HCl, and extracted with ethyl acetate. The organic extracts were dried, filtered and concentrated in vacuo to a white solid which was recrystallized twice from ethyl acetate to afford the title compound.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. customThe organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a white solid which
  6. customwas recrystallized twice from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a33709a5bc914e348b8470f1ef3ae1ab
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04912231

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