Trifluoroacetic acid → 3-[3-(2-Amino-2-methyl-propyl)phenyl]-acrylic acid benzyl ester

HRID 1866550Notes

Reaction equation

HRID 1866550 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19]([NH:22]C(OC(C)(C)C)=O)([CH3:21])[CH3:20])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9](=[O:30])[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19]([NH2:22])([CH3:20])[CH3:21])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 690235023-[3-(2-tert-Butoxycarbonylamino-2-methyl-propyl)-phenyl]-acrylic acid benzyl ester

Product 1

HCID 690261303-[3-(2-Amino-2-methyl-propyl)phenyl]-acrylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-phenyl]-acrylic acid benzyl ester (preparation 141), (2.23 g, 5.45 mmol), and trifluoroacetic acid (5 mL) in dichloromethane (10 mL) was stirred for 1 hour at room temperature. The mixture was then concentrated in vacuo and the residue was diluted with sodium hydrogen carbonate solution (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic solution was dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a yellow oil in quantitative yield.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additionthe residue was diluted with sodium hydrogen carbonate solution (10 mL)
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic solution was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3506092baba04f239831d82bb5456718
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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