4-Methylmorpholine → Boc-Ala-Ala-NH-(CH2)3-OH

HRID 76319

Reaktionsgleichung

Reaktionsgleichung von HRID 76319
[C:1]([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([C:16]([OH:18])=O)[CH3:15])=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.[NH2:26][CH2:27][CH2:28][CH2:29][OH:30]>C1COCC1>[NH:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C@H:9]([C:11]([NH:13][C@H:14]([C:16]([NH:26][CH2:27][CH2:28][CH2:29][OH:30])=[O:18])[CH3:15])=[O:12])[CH3:10]

Komponenten

5

Edukt 3

HCID 79724-Methylmorpholine2×HCID 90863-Amino-1-propanolHCID 6992569N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine

Produkt 1

HCID 59479657Boc-Ala-Ala-NH-(CH2)3-OHAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a vigorously stirring solution of Boc-(Ala)2-OH (1.55 gm, 5.96 mmol) and NMM (0.98 mL, 8.9 mmol) in THF (15 mL) cooled to −15° C. was added under an atmosphere of N2 ethyl chloroformate (ECF) (587 μL, 6.14 mmol). After stirring for 2 min, a solution of H2N(CH2)3OH (546 uL, 7.2 mmol) in THF (5 mL) was added to the mixture followed by NMM (1.64 mL, 14.9 mmol) and the mixture was warmed to r.t. and stirred until silica gel TLC indicated complete consumption of the starting acid (eluting solvent-MeOH:DCM—1:10, Rf—0.5) (˜8 h). The solvent was evaporated, and the residue was diluted with EtOAc and washed with brine, water, saturated solutions of citric acid and NaHCO3, and the organic layer was dried using NaHSO4, and the solvent was removed under vacuum to yield a residue which was purified using silica gel flash column chromatography—Hexanes:EtOAc—1:4; to give the desired product in 84% yield (1.59 g) as a solid, m.p.—142° C.

Aufarbeitung

  1. additionwas added under an atmosphere of N2 ethyl chloroformate (ECF) (587 μL, 6.14 mmol)
  2. stirringstirred until silica gel
  3. customconsumption of the starting acid (eluting solvent-MeOH:DCM—1:10, Rf—0.5) (˜8 h)
  4. customThe solvent was evaporated
  5. additionthe residue was diluted with EtOAc
  6. washwashed with brine, water, saturated solutions of citric acid and NaHCO3
  7. customthe organic layer was dried
  8. customthe solvent was removed under vacuum
  9. customto yield a residue which
  10. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-b033a9c4a8184099ba6d29d17aaf0d1a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835602B2

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