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

HRID 1879812

Reaction equation

HRID 1879812 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

HCID 86635763Tert-butyl 2-{N-[1,3-bis(acetyloxy)propan-2-yl]acetamido}acetateYield 50.3%

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fecacc3d785046c3a7638c8d4d1efd4f
Source dataset
uspto-grants-2012_11
Patent number
US08318705B2

Linked notes

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