[(2-Benzyloxy-4-chlorophenyl)-tert-butoxycarbonylamino]-acetic Acid Methyl Ester → (2-Benzyloxy-4-chlorophenylamino)-acetic Acid Methyl Ester

HRID 660824Notes

Reaction equation

HRID 660824 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][N:5]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)C(OC(C)(C)C)=O>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:28])[CH2:4][NH:5][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 1

HCID 68838982[(2-Benzyloxy-4-chlorophenyl)-tert-butoxycarbonylamino]-acetic Acid Methyl Ester

Product 1

HCID 68837988(2-Benzyloxy-4-chlorophenylamino)-acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of [(2-benzyloxy-4-chlorophenyl)-tert-butoxycarbonylamino]-acetic acid methyl ester (14.95 g, 36.8 mmol) in 180 mL of TFA/methylene chloride (1:2) is stirred at RT for 45 min. The solvent is removed under reduced pressure and the residue is dissolved in EtOAc (500 mL). To this solution is added diisopropylethylamine (13.11 g) and the resulting precipitate is filtered. The filtrate is evaporated to give the title compound as a tan solid. (M+1)=306.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue is dissolved in EtOAc (500 mL)
  3. additionTo this solution is added diisopropylethylamine (13.11 g)
  4. filtrationthe resulting precipitate is filtered
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-8ebd23000a914842b7dca2836e4356df
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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