Hydrochloric Acid → HCID 131731778, compound

HRID 2406849Notes

Reaction equation

HRID 2406849 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:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>O.ClCCl>[OH:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C@H:5]([NH:6][C:24](=[O:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:4]([O:3][CH3:2])=[O:15])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 76956Methyl tyrosinate hydrochloride

Product 1

HCID 131731778HCID 131731778, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

300 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 27.49 g of palmitoyl chloride (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 500 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 (39.4 g, 90.8% yield).

Workup

  1. additionwas added
  2. customto 0° C.
  3. extractionfollowed by extraction with 500 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-1b521936110c4042a18342a128d3ba3a
Source dataset
uspto-grants-2014_08
Patent number
US08809390B2

Reaction notes

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