Ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoate → ethyl 4-[N-(2-benzyloxy-5-bromophenethyl)amino]benzoate

HRID 355810Notes

Reaction equation

HRID 355810 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16][C:17]([NH:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.Cl.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16][CH2:17][NH:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 54475189Ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoate

Product 1

HCID 22675521ethyl 4-[N-(2-benzyloxy-5-bromophenethyl)amino]benzoateYield 57.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of ethyl 4-[2-benzyloxy-5-bromophenylacetamido]-benzoate (2.5 g) and BH3. THF (10 mM) in THF (60 ml) was stirred at 50° C. for 2 hours, cooled (ice bath) and diluted with 2N HCl solution (10 ml) and diethyl ether (50 ml). The organic layer was separated, dried (MgSO4) amd evaporated. The residue was purified by chromatography on silica gel eluting with dichloromethane to give ethyl 4-[N-(2-benzyloxy-5-bromophenethyl)amino]benzoate (1.4 g).

Workup

  1. temperaturecooled (ice bath)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4) amd
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-381aba25066f4f0496e223830cbc1bf9
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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