Glycine tert-butyl ester → Tert-butyl 2-{[1,3-bis(acetyloxy)propan-2-yl]amino}acetate

HRID 1630453노트

반응식

HRID 1630453 반응식
[C:1]([O:4][CH2:5][C:6](=O)[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].[NH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:9]([O:8][CH2:7][CH:6]([NH:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

참가 물질

4

반응물 3

HCID 151417Glycine tert-butyl esterHCID 2434181,3-DiacetoxyacetoneHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 86635762Tert-butyl 2-{[1,3-bis(acetyloxy)propan-2-yl]amino}acetate수율 38.7%

실험 절차

To a solution of 3-(acetyloxy)-2-oxopropyl acetate (3.0 g, 17.24 mmol) on dichloroethane (70 ml) was added tert-butyl 2-aminoacetate (2.35 ml, 17.24 mmol). The reaction was stirred for 90 minutes before sodium triacetoxyborohydride (5.5 g, 25.86 mmol) was added and stirring was continued for 18 hours. The reaction was quenched by the addition of saturated sodium hydrogen carbonate solution and the crude product was extracted into dichloromethane. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo. The title compound was purified by silica column chromatography eluting with 0-40% EtOAc:Hept to yield the title compound (1.93 g, 38% yield). 1H NMR (250 MHz, CHLOROFORM-d) δ 3.96-4.26 (4H, m), 3.30-3.45 (2H, m), 3.06 (1H, quin, 5.4 Hz), 2.09 (6H, s), 1.47 (9H, s).

후처리

  1. additionwas added
  2. customThe reaction was quenched by the addition of saturated sodium hydrogen carbonate solution
  3. extractionthe crude product was extracted into dichloromethane
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe title compound was purified by silica column chromatography
  9. washeluting with 0-40% EtOAc

출처 및 근거

ORD 기록
ord-ee187c311dc24d6b97db835572b2c9d2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791134B2

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