Hydrochloric Acid → O-Methyl-D-tyrosine--hydrogen chloride (1/1)

HRID 1763742Notes

Reaction equation

HRID 1763742 reaction equation
C([NH:4][C@@H:5]([C:15]([OH:17])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=O)C.O.[ClH:19]>CN(C=O)C>[ClH:19].[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([C:15]([OH:17])=[O:16])[NH2:4])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 11264873HCID 11264873, compound

Product 1

HCID 51358314O-Methyl-D-tyrosine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Acetyl-O-methyl-D-tyrosine, 24 g. is heated in 100 ml. of water and 100 ml. of concentrated hydrochloric acid for seven hours on a steam bath and let cool to room temperature overnight. The flask is swirled gently and the product crystallizes. It is separated by filtration, washed with a small amount of isopropanol, then with ether and dried to give 16.1 g. of the above named compound, [α]D23 +7.4° (c 2.02, DMF).

Workup

  1. temperatureis heated in 100 ml
  2. customthe product crystallizes
  3. customIt is separated by filtration
  4. washwashed with a small amount of isopropanol
  5. dry with materialwith ether and dried
  6. customto give 16.1 g

Sources & evidence

ORD record
ord-f74537e69b9c46fd969eace7bd4db216
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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