Hydrochloric Acid → L-Phenylalanine

HRID 2423002Notes

Reaction equation

HRID 2423002 reaction equation
COC1C=CC(C(C2C=CC(OC)=CC=2)(C2C=CC=CC=2)OCCCC(C)(OC([NH:19][C@@H:20]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([O:23]C)=[O:22])=O)C)=CC=1.O1CCCC1.[OH-].[Na+].Cl>CO>[NH2:19][C@H:20]([C:21]([OH:23])=[O:22])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59510439HCID 59510439, compound

Product 1

HCID 6140L-Phenylalanine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 2 (625 mg, 1 mmol), tetrahydrofuran (7 mL) and methanol (3 mL) was treated with 1N sodium hydroxide (1 mL, 1 mmol). The reaction mixture was stirred at room temperature for 6 hours then treated with 1N hydrogen chloride (1 mL, 1 mmol). The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried over ahydrous magnesium sulfate, and filtered. Evaporation of solvent afforded Cmoc-protected phenylalanine of sufficient purity for use in solid-supported peptide synthesis. MS (EI−): 610 (M−1).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over ahydrous magnesium sulfate
  4. filtrationfiltered
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-1ee091fe5c6c489fa2c98d4291f5745d
Source dataset
uspto-grants-2011_06
Patent number
US07960526B2

Reaction notes

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