Methane → Dl-Phenylalanine

HRID 1905819Notes

Reaction equation

HRID 1905819 reaction equation
[CH2:1]([CH:8]1[NH:12]C(=O)N[C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:15].[Na+].C.Cl>>[NH2:12][CH:8]([C:9]([OH:14])=[O:15])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 735655-(Phenylmethyl)-2,4-imidazolidinedione

Product 1

HCID 994Dl-PhenylalanineYield 72%

Procedure

95.1 g (0.5 mole) of 5-benzyl-hydantoin are heated to boiling in 350 ml of a 20% sodium hydroxide solution for 30 hours. The reaction mixture is clarified with activated charcoal and acidified with concentrated hydrochloric acid (pH 2). The precipitate (hydrantoinic acid) is filtered off and the phenyl alanine is precipitated from the filtrate as described in Example 11. Thus 59.5 g of the dry desired compound are obtained, yield 72%. Purity: 97.5% (according to HPLC).

Workup

  1. filtrationThe precipitate (hydrantoinic acid) is filtered off
  2. customthe phenyl alanine is precipitated from the filtrate
  3. dry with materialThus 59.5 g of the dry desired compound
  4. customare obtained

Sources & evidence

ORD record
ord-6e1f3bdc80a248e58d49025324ccd378
Source dataset
uspto-grants-1987_03
Patent number
US04647694

Reaction notes

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