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

HRID 70106

反応式

HRID 70106 の反応式
[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]

参加物

7

反応物 4

HCID 6328Methyl iodide2 回HCID 24758Sodium hydrideHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 2723922Sodium ethoxide2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1a7854345f3e4da0922298bdc2c9bd38
出典データセット
uspto-grants-2014_09
特許番号
US08822474B2

関連ノート

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