Trifluoroacetic acid → (S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide

HRID 2230275Notes

Reaction equation

HRID 2230275 reaction equation
CC(OC(=O)[NH:7][C@@H:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(C)C.F[C:25](F)(F)[C:26]([OH:28])=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:28][CH2:26][C:25]2[CH:18]=[CH:17][CH:16]=[CH:8][CH:9]=2)=[CH:21][CH:22]=1)[C:9]([NH:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11809380(S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl ester

Product 1

HCID 15517727(S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Example E ((S)-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester) (6.0 g, 14.1 mmol) in CH2Cl2 (28 mL) was treated with trifluoroacetic acid (28 mL). The resulting solution was stirred for 20 minutes and then concentrated. The residue was diluted with EtOAc (300 mL), washed with saturated bicarbonate solution (2×300 mL) and brine (300 mL), dried over Na2SO4, and concentrated to give 4.2 g (91%) of the title compound.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc (300 mL)
  3. washwashed with saturated bicarbonate solution (2×300 mL) and brine (300 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3ab293056ba4156b3e2b5414cedc1e2
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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