Methyl iodide → (2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acid

HRID 70106

반응식

HRID 70106 반응식
[H-].[Na+].[C:3]([NH:10][C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][OH:13])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[O-][CH2:18]C.[Na+].CI>C1COCC1.CO>[C:6]([O:5][C:3]([NH:10][C@@H:11]([CH2:12][O:13][CH3:18])[C:14]([OH:16])=[O:15])=[O:4])([CH3:9])([CH3:8])[CH3:7]

참가 물질

7

반응물 4

HCID 6328Methyl iodide2회HCID 24758Sodium hydrideHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 2723922Sodium ethoxide2회

생성물 1

HCID 7016354(2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Under nitrogen a mixture of 74 ml abs. THF and 6 ml abs. methanol is cooled to −70° C. and 2 g sodium hydride (55-65% dispersion) are added. The suspension is stirred for 0.4 hour at ambient temperature. Under nitrogen, 2.05 g N-Boc-L-serine are suspended in 100 ml abs. THF and 40 ml of the prepared sodium ethoxide solution are added. The suspension is stirred for 1 hour at ambient temperature and 1 ml methyliodide are added. After 1 hour the remainder of the sodium ethoxide solution and another 2 ml of methyliodide are added. After 18 hours the reaction mixture is evaporated to dryness. The residue is washed with water and ether and extracted. The water phase is acidified and extracted with ethyl acetate and dichloromethane. 0.52 g of the product are obtained.

후처리

  1. additionUnder nitrogen a mixture of 74 ml abs
  2. stirringThe suspension is stirred for 1 hour at ambient temperature
  3. customAfter 18 hours the reaction mixture is evaporated to dryness
  4. washThe residue is washed with water and ether
  5. extractionextracted
  6. extractionextracted with ethyl acetate and dichloromethane

출처 및 근거

ORD 기록
ord-1a7854345f3e4da0922298bdc2c9bd38
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822474B2

연결된 노트

불러오는 중…