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

HRID 1006049Notes

Reaction equation

HRID 1006049 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) and 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)
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-12c745bd5ccf4706a4b8b7853e63e94a
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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