Hydrochloric Acid → L-Phenylalanine

HRID 1976949Notes

Reaction equation

HRID 1976949 reaction equation
C[O:2][C:3](=[O:13])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].[OH-].[Na+].Cl>C(O)C>[NH2:5][C@H:4]([C:3]([OH:13])=[O:2])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 736234L-Phenylalanine, methyl ester

Product 1

HCID 6140L-PhenylalanineYield 179.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(2-chloro-6-methylbenzoyl)-4-[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine methyl ester (1.31 g, 2,6 mmol) in ethanol (45 mL) and 1.0 N sodium hydroxide 45 mL, 45 mmol) was stirred over night at room temperature to give a clear solution. The mixture was neutralized with 1 N hydrochloric acid to precipitate 1.28 g of a white solid. The mother liquor was extracted with ethyl acetate (2×50 mL) and the combined extracts were washed with sat. brine, dried (Na2SO4) and evaporated to give 0.56 g. Recrystallization of the first crop from ethyl acetate afforded N-(2-chloro-6-methylbenzoyl)-4-[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine (0.77 g). Recrystallization of the second crop from ethyl acetate afforded an additional 0.20 g. FAB HRMS: obs. mass 505.0483. Calcd mass, 505.0488 (M+H).

Workup

  1. customto give a clear solution
  2. customto precipitate 1.28 g of a white solid
  3. extractionThe mother liquor was extracted with ethyl acetate (2×50 mL)
  4. washthe combined extracts were washed with sat. brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give 0.56 g
  8. customRecrystallization of the first crop from ethyl acetate

Sources & evidence

ORD record
ord-74a9ad74b2bd41a2be14f883107d718f
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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