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

HRID 259003Notes

Reaction equation

HRID 259003 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 one 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 a 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 a room temperature in vacuo

Sources & evidence

ORD record
ord-e22ba5edc54d4d868a402207ff2e9cf2
Source dataset
uspto-grants-1977_07
Patent number
US04035507

Reaction notes

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