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

HRID 1630454노트

반응식

HRID 1630454 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8837a5af85da40e7af77e18cec4c8c74
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791134B2

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