Hydrochloric Acid → racemic N-chloroacetylisovaline

HRID 413350ノート

反応式

HRID 413350 の反応式
[NH2:1][C@:2]([C:6]([OH:8])=[O:7])([CH3:5])[CH2:3][CH3:4].[OH-].[Na+].[Cl:11][CH2:12][C:13](Cl)=[O:14].Cl>>[Cl:11][CH2:12][C:13]([NH:1][C@:2]([C:6]([OH:8])=[O:7])([CH3:5])[CH2:3][CH3:4])=[O:14]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide2 回HCID 2724877D-Isovaline

生成物 1

HCID 12009800racemic N-chloroacetylisovaline収率 78.5%

実験手順

To a well-stirred mixture chilled to 0° C. to 5° C. (ice bath) of racemic isovaline ((R,S) 2-amino-2-methylbutanoic acid) (350 g, 2.99 mole) and 2N aqueous sodium hydroxide (1.5 L) were added simultaneously chloroacetyl chloride (373 g, 3.31 mole) and 2N aqueous sodium hydroxide (1,718 ml, 3.44 mole) over 1.5 hours . The base was added at such a rate as to keep the reaction mixture basic at all times. The reaction mixture was warmed up to room temperature, treated with concentrated aqueous hydrochloric acid until acidic to litmus paper. A white solid formed which was separated by filtration and dried to yield 454 g (78.5%) of the expected racemic N-chloroacetylisovaline ((R,S) 2-chloroacetamido-2-methylbutanoic acid).

後処理

  1. additionThe base was added at such a rate as
  2. customA white solid formed which
  3. customwas separated by filtration
  4. customdried

出典と根拠

ORDレコード
ord-d7ef08130538433280d2d027af5f7a51
出典データセット
uspto-grants-2003_05
特許番号
US06566403B1

反応ノート

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