Hydrochloric Acid → HCID 131731777, compound

HRID 2406847Notes

Reaction equation

HRID 2406847 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:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O.ClCCl>[OH:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C@H:5]([NH:6][C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:4]([O:3][CH3:2])=[O:15])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 76956Methyl tyrosinate hydrochloride

Product 1

HCID 131731777HCID 131731777, compoundYield 93.6%

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 16.6 ml of octanoyl 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 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 separation by column chromatograph using hexane and ethyl acetate (Hex:EA=2:1), thereby obtaining a white solid (30.1 g, 93.3% yield).

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
  7. customfollowed by separation by column chromatograph

Sources & evidence

ORD record
ord-677469b101824c8283b03453d9833f25
Source dataset
uspto-grants-2014_08
Patent number
US08809390B2

Reaction notes

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