Hydrochloric Acid → HCID 69316412, compound

HRID 1393383Notes

Reaction equation

HRID 1393383 reaction equation
FC(F)(F)C(O)=O.C[O:9][C:10](=[O:40])[C@H:11]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)[CH:22]=1)[NH:12]C(OC(C)(C)C)=O.O.[OH-].[Li+].Cl>C(Cl)Cl.O>[CH:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:38]=[CH:39][C:30]=1[CH2:29][CH2:28][O:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][C@@H:11]([C:10]([OH:40])=[O:9])[NH2:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 168937Lithium hydroxide, monohydrateHCID 69321292HCID 69321292, compound

Product 1

HCID 69316412HCID 69316412, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) was added to a solution of N-t-butoxycarbonyl-3-[2-(2-naphthyl)ethoxy]-L-phenylalanine methyl ester (125 mg, 0.278 mmol) in methylene chloride (3 ml) under ice cooling and the mixture was stirred at the same temperature for 30 min. The solvent of the reaction mixture was distilled off at room temperature under reduced pressure. The residue was triturated with n-hexane and collected by filtration. The resultant solid was dissolved in tetrahydrofuran (1.2 ml)-water (0.6 ml). Lithium hydroxide mono-hydrate (41 mg, 0.973 mmol) was added to the solution with stirring under ice cooling and the mixture was reacted at the same temperature for 12 hrs. The reaction mixture was diluted with water (2 ml) and adjusted to pH 3-4 with 1N HCl. After the addition of water (25 ml), the mixture was stirred at room temperature for 1 hr. The precipitates were collected by filtration, washed with water and then dried under reduced pressure to give 3-[2-(2-naphthyl)ethoxy]-L-phenylalanine (55 mg, 59%) as colorless crystals.

Workup

  1. distillationThe solvent of the reaction mixture was distilled off at room temperature under reduced pressure
  2. customThe residue was triturated with n-hexane
  3. filtrationcollected by filtration
  4. dissolutionThe resultant solid was dissolved in tetrahydrofuran (1.2 ml)-water (0.6 ml)
  5. stirringwith stirring under ice cooling
  6. customthe mixture was reacted at the same temperature for 12 hrs
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. filtrationThe precipitates were collected by filtration
  9. washwashed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-6190af70fc6446859ebb372b25e31c4f
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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