1-Hydroxybenzotriazole → tert-Butyl 6-benzyloxy-3-(methoxymethylcarbamoyl)hexanoate

HRID 1912073

Reaktionsgleichung

Reaktionsgleichung von HRID 1912073
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([O-:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN[O:27][CH3:28].C1C=CC2N(O)N=[N:35][C:33]=2C=1.CCN=C=NCCCN(C)C.Cl>O.CN(C=O)C.C(N(CC)CC)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:13](=[O:15])[NH:35][CH2:33][O:27][CH3:28])[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866750434-tert-Butyl 2-(3-benzyloxypropyl)succinate

Produkt 1

HCID 71114707tert-Butyl 6-benzyloxy-3-(methoxymethylcarbamoyl)hexanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-tert-Butyl 2-(3-benzyloxypropyl)succinate (80 g), triethylamine (48.4 mL) and DMF (400 mL) were mixed. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (31.5 g), HOBt.H2O (45.6 g) and WSC.HCl (57.1 g) at ice temperature. The mixture was stirred at RT overnight. To the reaction mixture was added water (400 mL), and the mixture was extracted with hexane (480 mL, 480 mL, 240 mL). The combined organic layer was washed with aqueous 10 w/v % sodium carbonate (240 mL×3), aqueous 10 w/v % potassium hydrogen sulfate (240 mL), water (240 mL) and brine (240 mL), then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (84.1 g) as a crude product.

Aufarbeitung

  1. extractionthe mixture was extracted with hexane (480 mL, 480 mL, 240 mL)
  2. washThe combined organic layer was washed with aqueous 10 w/v % sodium carbonate (240 mL×3), aqueous 10 w/v % potassium hydrogen sulfate (240 mL), water (240 mL) and brine (240 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-02b0ae7dd9114c44b291f09a85f9c779
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604069B2

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