Pyruvic Acid → (2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

HRID 1445712ノート

反応式

HRID 1445712 の反応式
Cl.[CH2:2]([O:4][C:5](=[O:11])[C@H:6]([CH2:8][CH2:9][CH3:10])[NH2:7])[CH3:3].[OH-].[Na+].[C:14]([OH:19])(=[O:18])[C:15]([CH3:17])=O>C(O)C.[Pd]>[C:5]([C@@H:6]([NH:7][C@H:15]([C:14]([OH:19])=[O:18])[CH3:17])[CH2:8][CH2:9][CH3:10])([O:4][CH2:2][CH3:3])=[O:11]

参加物

6

反応物 3

HCID 1060Pyruvic AcidHCID 14798Sodium HydroxideHCID 12631224L-Norvaline, ethyl ester, hydrochloride (1:1)

生成物 1

HCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid収率 50.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒3 回

実験手順

L-Norvaline ethyl ester hydrochloride (50 gm) was dissolved in ethanol (600 ml). Sodium hydroxide (15.4 gm) dissolved in ethanol (500 ml) was added to the above at 10° C. and stirred for 30 minutes. Pyruvic acid (34.5 gm) solution in ethanol (200 ml) was then added to above reaction mass at 10° C. and stirred for 30 minutes. The reaction mass was then transferred to a hydrogenator along with 10% palladium on carbon (5 gm) and hydrogenated at 7 bar for 8 hours. The contents were filtered over celite and washed with ethanol (200 ml). The filtrate was concentrated completely under vacuum at about 50° C. Acetone (800 ml) was added to the residue and the contents refluxed for 1 hour and then cooled to room temperature and filtered to obtain the product (30 gm) as white crystals.

後処理

  1. additionwas added to the above at 10° C.
  2. stirringstirred for 30 minutes
  3. filtrationThe contents were filtered over celite
  4. washwashed with ethanol (200 ml)
  5. concentrationThe filtrate was concentrated completely under vacuum at about 50° C
  6. additionAcetone (800 ml) was added to the residue
  7. temperaturethe contents refluxed for 1 hour
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-0b083cf0231345e99b7a4705e7f8b55d
出典データセット
uspto-grants-2010_02
特許番号
US07666896B2

反応ノート

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