Trifluoroacetic acid → 2-({4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenylamino}-methyl)-benzoic acid ethyl ester

HRID 352443Notes

Reaction equation

HRID 352443 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][N:12](C(OC(C)(C)C)=O)[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])=[CH:15][CH:14]=1)[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:41])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])=[CH:15][CH:14]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 694866072-[(Tert-butoxycarbonyl-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-amino)-methyl]-benzoic acid ethyl ester

Product 1

HCID 694867732-({4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenylamino}-methyl)-benzoic acid ethyl esterYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.00 g of 2-[(tert-butoxycarbonyl-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-amino)-methyl]-benzoic acid ethyl ester in 40 ml of dichloromethane was added 9.6 ml of trifluoroacetic acid and stirring was continued at 22° C. for 2.5 h. The mixture was partitioned between aqueous saturated Na2CO3 and dichloromethane, the organic layer was dried and evaporated. The residue was purified by chromatography (SiO2, n-hexane/AcOEt 4:1) to give 3.14 g of the title compound as a pale yellow oil. MS: (M+H)+ 457.5.

Workup

  1. customThe mixture was partitioned between aqueous saturated Na2CO3 and dichloromethane
  2. customthe organic layer was dried
  3. customevaporated
  4. customThe residue was purified by chromatography (SiO2, n-hexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-5e015b575c3b40538ee061dc414e83a1
Source dataset
uspto-grants-2004_06
Patent number
US06747049B2

Reaction notes

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