Acetyl chloride → Tert-butyl 2-{N-[1,3-bis(acetyloxy)propan-2-yl]acetamido}acetate

HRID 1630454

Reaktionsgleichung

Reaktionsgleichung von HRID 1630454
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:8][CH2:9][CH:10]([NH:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:11][O:12][C:13](=[O:15])[CH3:14])(=[O:7])[CH3:6].C(N(CC)CC)C>>[C:5]([O:8][CH2:9][CH:10]([N:16]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:1](=[O:3])[CH3:2])[CH2:11][O:12][C:13](=[O:15])[CH3:14])(=[O:7])[CH3:6]

Komponenten

4

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86635762Tert-butyl 2-{[1,3-bis(acetyloxy)propan-2-yl]amino}acetate

Produkt 1

HCID 86635763Tert-butyl 2-{N-[1,3-bis(acetyloxy)propan-2-yl]acetamido}acetateAusbeute 50,3 %

Versuchsvorschrift

Acetyl chloride (0.357 ml, 5.0 mmol) was added dropwise to a stirred solution of tert-butyl 2-{[1,3-bis(acetyloxy)propan-2-yl]amino}acetate (1.22 g, 4.2 mmol) and triethylamine (0.696 ml, 5.0 mmol). After 2 hours the reaction was quenched by the addition of water. The organic phase was separated and washed with further aliquots of water before being dried over MgSO4, filtered and concentrated in vacuo. The title compound was purified by silica column chromatography eluting with 25% EtOAc:Hept to yield the title compound (0.7 g, 50%). 1H NMR (250 MHz, CHLOROFORM-d) δ 4.04-4.44 (5H, m), 3.98 (1H, s), 3.88 (1H, s), 2.08 (3H, s), 2.05 (6H, s), 1.47 (9H, s).

Aufarbeitung

  1. customAfter 2 hours the reaction was quenched by the addition of water
  2. customThe organic phase was separated
  3. washwashed with further aliquots of water
  4. dry with materialbefore being dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe title compound was purified by silica column chromatography
  8. washeluting with 25% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-8837a5af85da40e7af77e18cec4c8c74
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791134B2

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