Hydrochloric Acid → (S)-2',6'-Dimethyltyrosine hydrochloride

HRID 1638426Notes

Reaction equation

HRID 1638426 reaction equation
C[O:2][C:3](=[O:19])[C@H:4]([CH2:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([OH:17])=[CH:12][C:11]=1[CH3:18])[NH:5]C(=O)C.[ClH:20]>>[ClH:20].[CH3:16][C:15]1[CH:14]=[C:13]([OH:17])[CH:12]=[C:11]([CH3:18])[C:10]=1[CH2:9][C@@H:4]([C:3]([OH:19])=[O:2])[NH2:5]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 53859400HCID 53859400, compound2×

Product 1

HCID 44607638(S)-2',6'-Dimethyltyrosine hydrochloride

Procedure

2,6-Dimethyl-(S)-Tyrosine hydrochloride was prepared by deprotecting N-acetyl-2,6-dimethy-(S)-tyrosine methyl ester as follows: In a 100 ml round-bottom flask was placed 3.40 g (13 mmol) of N-acetyl-2,6-dimethyl-(S)-tyrosine methyl ester and 20 mL of 6N hydrochloric acid. The reaction mixture was refluxed under argon for 41/2 hours, cooled and then concentrated under reduced pressure to afford 3.48 g of a white solid; 1H NMR analysis indicated: (δ, CD3OD) 6.35 (s, 2H), 3.90 (t, J=7 Hz, 1H), 3.3-3.0 (m, 2H) and 2.21 (s, 6H). Mass spectrum analysis indicated: (m/e) 209 (M+), 135 (100%) and 91.

Workup

  1. customIn a 100 ml round-bottom flask was placed
  2. temperatureThe reaction mixture was refluxed under argon for 41/2 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e0b087f11d74113b72fa4ab99fca968
Source dataset
uspto-grants-1989_11
Patent number
US04879398

Reaction notes

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