Nitric Acid → (S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-3-nitro-phenyl)-propionic acid methyl ester

HRID 1358596

Reaction equation

HRID 1358596 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[N+:22]([O-])([OH:24])=[O:23]>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 7019130Boc-Tyr-OMe

Product 1

HCID 15518593(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-3-nitro-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-L-tyrosine methyl ester (5.64 g) in THF (10 ml) was added NH4NO3 (3 g) and concentrated HNO3 (3 ml). After 30 sec., the reaction mixture turned to dark red with reflux occurring. The reaction mixture was quenched with solid NaHCO3 and H2O, and extracted with AcOEt. The extract was dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluent; Hexane→1:1, Hexane/AcOEt) to give N-(tert-butoxycarbonyl)-3-nitro-L-tyrosine methyl ester (3.42 g). The obtained compound was treated in a similar manner as described in R. Example 4 to give 3-Nitro-L-tyrosine methyl ester, hydrochloride salt.

Workup

  1. temperaturewith reflux
  2. customThe reaction mixture was quenched with solid NaHCO3 and H2O
  3. extractionextracted with AcOEt
  4. dry with materialThe extract was dried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluent; Hexane→1:1, Hexane/AcOEt)

Sources & evidence

ORD record
ord-50bfa75144c34bf7995b8cf121ecb483
Source dataset
uspto-grants-2003_07
Patent number
US06596752B1

Linked notes

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