Sulfuric Acid → Benzyloxycarbonylamino-(4-methoxy-3-methyl-phenyl)-acetic acid

HRID 2222982

Reaction equation

HRID 2222982 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12](O)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25].S(=O)(=O)(O)O>C(O)(=O)C>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:22]1[CH:21]=[CH:20][C:19]([O:24][CH3:25])=[C:18]([CH3:17])[CH:23]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 336372-MethylanisoleHCID 35095062-(((Benzyloxy)carbonyl)amino)-2-hydroxyacetic acid

Product 1

HCID 68798586Benzyloxycarbonylamino-(4-methoxy-3-methyl-phenyl)-acetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of benzyloxycarbonylamino-hydroxy-acetic acid (5.9 g, 26.2 mmol) (prepared according to the procedure of E. H. W. Bohme, et al., J. Med. Chem, 1980, 23, 405-412) and 2-methylanisole (3.2 g, 26.2 mmol) in acetic acid (150 mL) was added concentrated sulfuric acid (15 mL). The mixture was stirred at room temperature for 1 hour, then poured into ice/water and extracted with ethyl acetate (2×200 mL). The combined organic extracts were dried over sodium sulfate and concentrated to give an oily residue. The residue was triturated in hexanes, the precipitate formed was collected by filtration and dried overnight to give crude benzyloxycarbonylamino-(4-methoxy-3-methyl-phenyl)-acetic acid as a white solid (8.6 g, 100%).

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated
  4. customto give an oily residue
  5. customThe residue was triturated in hexanes
  6. customthe precipitate formed
  7. filtrationwas collected by filtration
  8. customdried overnight

Sources & evidence

ORD record
ord-789344fc26cb45b19583704352d755b1
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Linked notes

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