Hydrochloric Acid → HCID 44176960, compound

HRID 2406848Notes

Reaction equation

HRID 2406848 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:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>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:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 76956Methyl tyrosinate hydrochloride

Product 1

HCID 44176960HCID 44176960, compoundYield 90.6%

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 21.88 g of dodecanoyl 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 separation by column chromatograph using hexane and ethyl acetate (Hex:EA=2:1), thereby obtaining a white solid (34.2 g, 90.5% 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
  7. customfollowed by separation by column chromatograph

Sources & evidence

ORD record
ord-e561a9c6320143ed9a1a6ee5b0df7f06
Source dataset
uspto-grants-2014_08
Patent number
US08809390B2

Reaction notes

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