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4-Methylmorpholine → Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybutanoate

HRID 538921
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 538921
[CH2:1]([O:8][C:9](=[O:23])[CH2:10][C@@H:11]([C:20](O)=[O:21])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.[BH4-].[Na+]>COCCOC>[CH2:1]([O:8][C:9](=[O:23])[CH2:10][C@H:11]([NH:12][C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:20][OH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl esterHCID 4311764Sodium borohydride

Produkt 1

HCID 10040985Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8071
1,2-Dimethoxyethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a solution of Boc-L-aspartic acid-4-benzyl ester (100 g, 309 mmol) in DME (1.8 L) at −20° C. was added NMM (34 mL, 309 mmol) then dropwise iso-butylchloroformate (40 mL, 309 mmol) and the mixture was stirred at −20° C. for 20 min. The reaction mixture was filtered and the filtrate was cooled to −20° C. NaBH4 (17.5 g, 463 mmol) was added portionwise at −20° C. The mixture was allowed to warm and stirred at rt for 1 h. The mixture was quenched with a 20% citric acid solution and then extracted with AcOEt. The organic layer was washed with NaHCO3 solution, H2O and brine, dried (MgSO4), filtered and concentrated. The product was used without further purification for the next step.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. temperatureto warm
  3. customThe mixture was quenched with a 20% citric acid solution
  4. extractionextracted with AcOEt
  5. washThe organic layer was washed with NaHCO3 solution, H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was used without further purification for the next step

Quellen und Nachweise

ORD-Eintrag
ord-379a98ce8165465aad03657a829ab132
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08865894B2

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