Sodium Hydroxide → (2S)-4-[bis(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamothioyl]-2-{[(tert-butoxy)carbonyl]amino}butanoic acid

HRID 1923974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1923974
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:12]([CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]([O:19]C)=[O:18])=[S:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:35]([O:34][C:32]([NH:31][CH2:30][CH2:29][N:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:12]([CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:17]([OH:19])=[O:18])=[S:13])=[O:33])([CH3:36])([CH3:37])[CH3:38]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59366732methyl (2S)-4-[bis(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamothioyl]-2-{[(tert-butoxy) carbonyl]amino}butanoate

Produkt 1

HCID 59366983(2S)-4-[bis(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamothioyl]-2-{[(tert-butoxy)carbonyl]amino}butanoic acidAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To the solution of the ester XV (290 mg, 0.51 mmol) in MeOH (10 mL) was added 4 M NaOH dropwise until pH=13. The mixture was stirred overnight at r.t. before evaporating the MeOH under reduced pressure. The residue was mixed with water and washed with ether. After acidifying to pH˜3 with 2 M HCl, the product was extracted with DCM, dried over MgSO4 and concentrated under vacuum to give (2S)-4-[bis(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamothioyl]-2-{[(tert-butoxy)carbonyl]amino}butanoic acid XVI (250 mg, 0.45 mmol, 88% yield). ESIMS found for C24H44N4O8S m/z 549 (M+H).

Aufarbeitung

  1. custombefore evaporating the MeOH under reduced pressure
  2. additionThe residue was mixed with water
  3. washwashed with ether
  4. extractionthe product was extracted with DCM
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-098228d0c9694843b46de188715445b8
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178490B2

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