Triethylamine → O-Acetyl-3-(acetyloxy)-L-tyrosine

HRID 462213Notes

Reaction equation

HRID 462213 reaction equation
Cl.[C:2]([O:5][C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][C:17]=1[O:18][C:19](=[O:21])[CH3:20])[CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])(=[O:4])[CH3:3].C(N(CC)CC)C>CO.ClCCl>[C:2]([O:5][C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][C:17]=1[O:18][C:19](=[O:21])[CH3:20])[CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])(=[O:4])[CH3:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 23620469HCID 23620469, compound

Product 1

HCID 23620470O-Acetyl-3-(acetyloxy)-L-tyrosineYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3,4-diacetyloxy-L-phenylalanine hydrochloride (15.00 g, 47.2 millimole) was dissolved in 20 ml of methanol and diluted to 900 ml with dichloromethane. To this solution, there was added, with vigorous stirring, 4.80 g (47.5 millimole) of triethylamine, which caused a gelatinous mass to form. After 1 hour, this mass was filtered and the residue was suspended in dichloromethane (300 ml) and filtered again. The residue was still contaminated with triethylamine hydrochloride. Consequently, it was suspended in dichloromethane (300 ml) again, and stirred for 3.5 hours. The suspension was filtered and dried at room temperature in vacuo to yield 12.5 g (95% yield by nmr) of 3,4-diacetyloxy-L-phenylalanine.

Workup

  1. customto form
  2. filtrationthis mass was filtered
  3. filtrationfiltered again
  4. filtrationThe suspension was filtered
  5. customdried at room temperature in vacuo

Sources & evidence

ORD record
ord-5f87db2385b94939a101547cec0fa9fa
Source dataset
uspto-grants-1977_12
Patent number
US04065566

Reaction notes

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