Methanol → N-Acetyl-L-phenylalanine

HRID 436351

Reaction equation

HRID 436351 reaction equation
C(P(C1C=CC=CC=1)CCP(CC1C(OC)=CC=CC=1)C1C=CC=CC=1)C1C(OC)=CC=CC=1.CO.[C:37]([NH:40][C:41](=[CH:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:42]([OH:44])=[O:43])(=[O:39])[CH3:38].[H][H]>C(O)(C)C>[C:37]([NH:40][C@H:41]([C:42]([OH:44])=[O:43])[CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 887MethanolHCID 956312-(Acetylamino)-3-phenyl-2-propenoic acidHCID 150615581,2-Bis(o-anisylphenylphosphino) ethaneHCID 178418361HCID 178418361, compound

Product 1

HCID 74839N-Acetyl-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 0.013 g. of [Rh(COD)Cl]2 (.026 m moles) and 0.024 g. 1,2-bis(o-anisylphenylphosphino) ethane prepared in Example 1 (0.051 m moles) in 5 ml. of methanol was made with stirring for 15 minutes at 25° C. With careful exclusion of air, 0.5 ml. of this solution was added to a slurry of 1.00 g. of α-acetamidocinnamic acid in 25 ml. of 88% i-propanol at 50° C. and the resulting mass was subjected to 3.5 atm. (abs. pressure) of hydrogen. The hydrogenation reaction was completed in 0.7 hours. N-acetyl-L-phenylalanine can be isolated from the reaction mass by crystallization. Analysis of the reaction mixture showed that an optical purity of 92.8% of the L isomer was obtained.

Workup

  1. additionof this solution was added to a slurry of 1.00 g
  2. customat 50° C.
  3. customThe hydrogenation reaction
  4. waitwas completed in 0.7 hours

Sources & evidence

ORD record
ord-76509d7ecc004512b734f8bc7bf057e7
Source dataset
uspto-grants-1977_02
Patent number
US04008281

Linked notes

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