Acetyl chloride → Methyl 3-nitro-L-tyrosinate--hydrogen chloride (1/1)

HRID 2289417Notes

Reaction equation

HRID 2289417 reaction equation
[C:1]([Cl:4])(=O)C.[N+:5]([C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][C:19]=1[OH:20])[CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])([O-:7])=[O:6]>CO>[ClH:4].[CH3:1][O:15][C:14](=[O:16])[C@H:12]([CH2:11][C:10]1[CH:17]=[CH:18][C:19]([OH:20])=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=1)[NH2:13]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 651243-Nitro-L-tyrosine

Product 1

HCID 69941840Methyl 3-nitro-L-tyrosinate--hydrogen chloride (1/1)Yield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (8.9 ml, 125 mmol) was added slowly to methanol (100 ml) at 0°. 3-Nitro-L-tyrosine (5.65 g, 25 mmol) was added and the mixture refluxed for 2 h. The solvent was evaporated in vacuo and the yellow solid obtained recrystallised from methanol to give the title compound as yellow needles (2.97 g, 43%), m.p. 200-201°. (Found: C, 43.29;H, 4.69; N, 10.19. C10H12N2O5HCl requires C, 43.41;H, 4.74; N, 10.13%); δH (CD3OD) 8.00 (1H, d, J 2.2 Hz, ArH), 7.53 (1H, dd, J 2.3, 8.6 Hz, ArH), 7.17 (1H, d, J 8.6 Hz, ArH), 4.37 (1H, dd, J 6.4, 7.0 Hz, CHα), 3.83 (3H, s, CO2CH3), 3.29 (1H, dd, J 6.3, 14.6 Hz, CHAHBAr) and 3.20 (1H, dd, J 7.1, 14.6 Hz, CHAHBAr); m/z (ES, 27V) 241 (M+ +1).

Workup

  1. temperaturethe mixture refluxed for 2 h
  2. customThe solvent was evaporated in vacuo
  3. customthe yellow solid obtained
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-5a17ed3629144b309cf591897a6db66c
Source dataset
uspto-grants-2000_07
Patent number
US06093696

Reaction notes

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