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Lithium Hydroxide → (4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]-L-proline

HRID 884036
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 884036
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:22](=[O:24])[CH3:23])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:25]([O:27]C)=[O:26])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[OH-]>CO.O>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:22](=[O:24])[CH3:23])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:25]([OH:27])=[O:26])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]
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Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 67359765Methyl(2S,4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate

Produkt 1

HCID 67357391(4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]-L-prolineAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962Water
Lösungsmittel

Versuchsvorschrift

Methyl (2S,4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate (0.98 g, 2.47 mmol) obtained in Step B, was dissolved in MeOH (8 mL) and water (1.6 mL). LiOH (0.18 g, 7.52 mmol) was added thereto at 0˜5° C. After the reaction mixture was stirred at room temperature for 3 hours and concentrated in vacuo, the obtained residue was diluted with water and the solution was extracted with EtOAc. The extracted organic solution was washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (0.92 g, 97%).

Aufarbeitung

  1. customat 0˜5° C
  2. concentrationconcentrated in vacuo
  3. additionthe obtained residue was diluted with water
  4. extractionthe solution was extracted with EtOAc
  5. washThe extracted organic solution was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4cc2e667eaea4ac5b501ef8d722a7a38
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08236955B2

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