Ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate → Ethyl 2-(2-amino-3-phenylpropanoyloxy)benzoate

HRID 919155Notes

Reaction equation

HRID 919155 reaction equation
C(OC([NH:8][CH:9]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:10]([O:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:11])=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:8][CH:9]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:10]([O:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:11]

Participants

4

Reactant 1

HCID 67173975Ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate

Product 1

HCID 59193288Ethyl 2-(2-amino-3-phenylpropanoyloxy)benzoateYield 69.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate (1.2 g, 2.9 mmol) was dissolved in CH2Cl2 (10 mL) and TFA (4 mL). The reaction was stirred (RT, 3 h) and then concentrated. The crude material was purified by silica chromatography (0-10% MeOH/CH2Cl2) to afford 0.63 g of ethyl 2-(2-amino-3-phenylpropanoyloxy)benzoate. Mass calculated for C18H19NO4=313.35. found: [M+H]+=314.1.

Workup

  1. concentrationconcentrated
  2. customThe crude material was purified by silica chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-703effadca0843a981a6d8ce391f45a7
Source dataset
uspto-grants-2016_03
Patent number
US09272984B2

Reaction notes

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