Hydrochloric Acid → N-[(Benzyloxy)carbonyl]-O-(trifluoromethyl)-L-tyrosine

HRID 1799298Notes

Reaction equation

HRID 1799298 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5].[CH2:19]([O:26][C:27](Cl)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O.Cl>[OH-].[Na+]>[CH2:19]([O:26][C:27]([NH:2][C@@H:3]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:12][CH:13]=1)[C:4]([OH:6])=[O:5])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10387Benzyl chloroformateHCID 69017088(S)-2-Amino-3-(4-(trifluoromethoxy)phenyl)propanoic acid hydrochloride

Product 1

HCID 69017443N-[(Benzyloxy)carbonyl]-O-(trifluoromethyl)-L-tyrosine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

(2S)-2-Amino-3-[4-(trifluoromethoxy)phenyl]propanoic acid hydrochloride (3 mg) prepared in Reference Example 3 (3b) was dissolved in 0.5 N sodium hydroxide (100 μL), and then (benzyloxy)carbonyl chloride (ZCl, 5 μL) was added thereto. The resulting mixture was stirred, and then water (100 μL) was added thereto. The resulting mixture was changed to acidic with 1 N hydrochloric acid (50 μL) and extracted with ethyl acetate (300 μL) to obtain the corresponding (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[4-(trifluoromethoxy)phenyl]propanoic acid. The optical purity was determined by HPLC under the following conditions.

Workup

  1. extractionextracted with ethyl acetate (300 μL)

Sources & evidence

ORD record
ord-447ef25ddde94896b942df72d3f249ab
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

Loading…