Hydrochloric Acid → HCID 70549678, compound

HRID 68004Notes

Reaction equation

HRID 68004 reaction equation
C[O:2][C:3](=[O:24])[C@:4]([CH:22]=[CH2:23])([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[NH:5]OCC1C=CC=CC=1.[ClH:25]>>[ClH:25].[CH:22]([C@@:4]([C:3]([OH:24])=[O:2])([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[NH2:5])=[CH2:23]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86737817HCID 86737817, compound

Product 1

HCID 70549678HCID 70549678, compound

Procedure

A mixture consisting of 0.554 g of benzyloxy-α-vinyltyrosine methyl ester and 40 ml of 6 N aqueous hydrochloric acid was heated at reflux with rapid stirring for 2 hours. The reaction mixture was cooled, extracted three times with 5 ml of methylene chloride and treated with activated charcoal. Filtration and evaporation of solvent gave 0.355 g of α-vinyltyrosine hydrochloride as an amorphous solid. NMR (D2O) showed: 3.35 (2H,AB, JAB =15, δAB =22), 5.55 (1H,d, J=18), 5.70 (1H,d,J=12), 6.43 (1H, d of d, J=18,12), 7.27 (2H,AB, JAB =9, δAB =22). m/e 207 (P-36).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted three times with 5 ml of methylene chloride
  5. additiontreated with activated charcoal
  6. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-fce57dbf616745dfb150214a97287a67
Source dataset
uspto-grants-1982_08
Patent number
US04347375

Reaction notes

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