Methanol → O-Methyl-D-tyrosine methyl ester HCl

HRID 1763743Notes

Reaction equation

HRID 1763743 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1.[CH3:16]O.S(Cl)([Cl:20])=O>N1C=CC=CC=1>[ClH:20].[CH3:16][O:12][C:11](=[O:13])[C@@H:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:15][CH:14]=1)[NH2:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 51358314O-Methyl-D-tyrosine--hydrogen chloride (1/1)

Product 1

HCID 24938358O-Methyl-D-tyrosine methyl ester HCl

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

O-Methyl-D-tyrosine hydrochloride, 10.0 g., in 100 ml. of methanol is cooled in an ice bath and treated slowly with 3.4 ml. of thionyl chloride. The reaction is stirred for one hour with cooling and then overnight at room temperature. The solution is evaporated to dryness and the residue crystallized from methanol-ether to give 5.2 g. of the above named compound mp. 189°-190° C., [α]D23 -68° (c 1.04, pyridine).

Workup

  1. additiontreated slowly with 3.4 ml
  2. temperaturewith cooling
  3. customovernight
  4. customat room temperature
  5. customThe solution is evaporated to dryness
  6. customthe residue crystallized from methanol-ether
  7. customto give 5.2 g

Sources & evidence

ORD record
ord-28de2ce7fb2245979a99bb6c0a0a76e0
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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