Hydrochloric Acid → racemic N-chloroacetylisovaline

HRID 413350노트

반응식

HRID 413350 반응식
[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]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide2회HCID 2724877D-Isovaline

생성물 1

HCID 12009800racemic N-chloroacetylisovaline수율 78.5%

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d7ef08130538433280d2d027af5f7a51
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566403B1

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