Trifluoroacetic acid → Methyl [2-methyl-4-(methylamino)phenoxy]acetate

HRID 1242300Notes

Reaction equation

HRID 1242300 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12](C(OC(C)(C)C)=O)[CH3:13])=[CH:8][C:7]=1[CH3:21].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[CH:8][C:7]=1[CH3:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67072167[4-(Tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester

Product 1

HCID 45097147Methyl [2-methyl-4-(methylamino)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude 25.8 g (77 mmol) of the above prepared [4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester in 600 ml CH2Cl2 was treated at 0° C. with 198 ml TFA and stirred at RT for 30 min. The reaction was evaporated and treated with chilled aqueous saturated NaHCO3 solution/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried over sodium sulfate, and evaporated to give 16.2 g of crude product. Purification by flash chromatography on SiO2 with a gradient of n-heptane: AcOEt (9:1 to 4:1) yielded 12.7 g of (2-methyl-4-methylamino-phenoxy)-acetic acid methyl ester as an orange oil.

Workup

  1. customThe reaction was evaporated
  2. additiontreated with chilled aqueous saturated NaHCO3 solution/Et2O (3×)
  3. washThe organic phases were washed with aqueous 10% NaCl
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give 16.2 g of crude product
  7. customPurification by flash chromatography on SiO2 with a gradient of n-heptane: AcOEt (9:1 to 4:1)

Sources & evidence

ORD record
ord-1221326d23ee4507a93b73f5adecdc97
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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