Water → (3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid

HRID 2193553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2193553
C(OC(N1CC[C@@H](NC2C=CC(N3C[C@H](CNC(=O)C)OC3=O)=CC=2F)C1)=O)(C)(C)C.C([O:34][C:35]([C@H:37]1[C@@H:41]([CH2:42][NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][N:39]([CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:38]1)=[O:36])C.O.[OH-].[Li+].O>C1COCC1>[CH2:51]([N:39]1[CH2:40][C@H:41]([CH2:42][NH:43][C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[C@H:37]([C:35]([OH:36])=[O:34])[CH2:38]1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67274345(3R)3-{4-[(5S)-5-(Acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenylamino}-pyrrolidine-1-carboxylic Acid Tert-Butyl EsterHCID 68420071(3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid Ethyl Ester

Produkt 1

HCID 68421821(3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 2.9 (3R, 4R) and (3S, 4S)-1-benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic acid ethyl ester (8.0 mmol) in 50 ml THF were added 671 mg lithium hydroxide mono hydrate (, 16 mmol) and 0.5 ml water. The solution was stirred at 40° C. and the reaction monitored by TLC. After 72 h the solvent was evaporated, the residue dissolved in dichloromethane, washed with water and brine, dried over Mg sulfate, filtered and evaporated. The residue was crystallized from a dichloromethane/hexane mixture.

Aufarbeitung

  1. customAfter 72 h the solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over Mg sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from a dichloromethane/hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-f406e256d96646acb6282da856e4a168
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329908B2

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