Water → (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxypropanoic acid

HRID 1867674ノート

反応式

HRID 1867674 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([O:15]C)=[O:14])[CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.[OH-].[Li+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([OH:15])=[O:14])[CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 71742038(R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methoxypropanoate

生成物 1

HCID 27281801(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxypropanoic acid収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl N-(tert-butoxycarbonyl)-O-methyl-D-serinate (2.0 g, 85.7 mmol) was dissolved in tetrahydrofuran (40 ml) and water (20 ml) and lithium hydroxide mono hydrate (1.8 g, 42.9 mmol) added. The mixture was stirred for 4 hours at room temperature, concentrated under reduced pressure to remove most of the tetrahydrofuran and then acidified by the addition of concentrated hydrochloric acid. The solution was extracted with ethyl acetate (three times). The combined organics were dried (MgSO4), filtered and evaporated under reduced pressure to give N-(tert-butoxycarbonyl)-O-methyl-D-serine (1.9 g, 100%) as a colourless oil; 1H NMR spectrum: (DMSO d6) 1.37 (s, 9H), 3.23 (s, 3H), 3.53 (m, 2H), 4.18 (m, 1H), 6.87 (d, 1H), 12.60 (brs, 1H).

後処理

  1. concentrationconcentrated under reduced pressure
  2. customto remove most of the tetrahydrofuran
  3. additionacidified by the addition of concentrated hydrochloric acid
  4. extractionThe solution was extracted with ethyl acetate (three times)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-90b50164703e43cfb1233d39d973295e
出典データセット
uspto-grants-2009_12
特許番号
US07632840B2

反応ノート

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