Hydrochloric Acid → N-Hexanoyltyrosine methyl ester

HRID 2406846Notes

Reaction equation

HRID 2406846 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.Cl.[C:24](Cl)(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O.ClCCl>[C:24]([NH:6][C@@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[C:4]([O:3][CH3:2])=[O:15])(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 76956Methyl tyrosinate hydrochloride

Product 1

HCID 56652925N-Hexanoyltyrosine methyl esterYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

200 ml of dichloro methane (DCM) was added to (L)-tyrosine methyl ester HCl salt (23.16 g, 0.1 mol), and 28 ml of triethyl amine (TEA, 0.2 mol) was added thereto, thereby dissolving HCl salt. The reactor was temperature-lowered to 0° C. by using an ice bath, and hexanoyl chloride (13.8 ml, 0.1 mol) was slowly added, following by stirring for 3-4 hours. 200 ml of water was added to the reacted material, followed by extraction with 400 ml of ethyl acetate. Drying over sodium sulfate followed by filtering was carried out. The solvent was removed from the filtrate by rotary evaporation, followed by solidification with hexane and ethyl acetate, thereby obtaining a white solid (27.1 g, 92.5% yield) [hereinafter, referred to as Compound 1a].

Workup

  1. additionwas added
  2. customto 0° C.
  3. extractionfollowed by extraction with 400 ml of ethyl acetate
  4. dry with materialDrying over sodium sulfate
  5. filtrationby filtering
  6. customThe solvent was removed from the filtrate by rotary evaporation

Sources & evidence

ORD record
ord-39ccf835aa3d4e098241e5f474bf1395
Source dataset
uspto-grants-2014_08
Patent number
US08809390B2

Reaction notes

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