Lithium hydroxide, monohydrate → L-Proline, N-(methoxycarbonyl)-L-valyl-5-methyl-, (5S)-

HRID 1625509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625509
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:20]([CH3:22])[CH3:21])[C:7]([N:9]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]1[C:15]([O:17]CC)=[O:16])=[O:8])=[O:4].O.[OH-].[Li+]>C(O)C>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:20]([CH3:22])[CH3:21])[C:7]([N:9]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]1[C:15]([OH:17])=[O:16])=[O:8])=[O:4]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 67411636(2S,5S)-ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate

Produkt 1

HCID 67412687L-Proline, N-(methoxycarbonyl)-L-valyl-5-methyl-, (5S)-Ausbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To an ice-cold stirred solution of ethyl (2S,5S)-1-[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidine-2-carboxylate (5.6 g, 17.8 mmol) in ethanol (18 ml) is added a solution of lithium hydroxide monohydrate (17.8 mL of 1.7 M, 30.3 mmol). The reaction mixture is stirred for 5 hours at rt. The reaction mixture is concentrated, diluted with water, washed with ether. The aqueous solution is acidified with aq. 1N HCl, extracted with CH2Cl2. The combined extracts are washed with brine, dried (Na2SO4), concentrated to afford (2S,5S)-1-[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidine-2-carboxylic acid (5 g, 94%) as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with water
  3. washwashed with ether
  4. extractionextracted with CH2Cl2
  5. washThe combined extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0245b5327b75455c9b3ebb6ffeed14d8
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08779156B2

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