Water → HCID 178472682, compound

HRID 910049Notes

Reaction equation

HRID 910049 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[CH:14]=O)[CH3:2].Cl.[CH2:18]([O:20][C:21](=[O:24])[CH2:22][NH2:23])[CH3:19].CCN(CC)CC.O>ClCCl>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1/[CH:14]=[N:23]/[CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:24])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 880259ethyl (4-bromo-2-formylphenoxy)acetateHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 178472682HCID 178472682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Bromo-2-formylphenoxyacetic acid ethyl ester (1.44 g, 5 mmol) was dissolved in dichloromethane (50 mL) and glycine ethyl ester hydrochloride (1.39 g, 10 mmol) as well as Et3N (1.4 mL, 10 mmol) was added. The mixture was stirred at room temperature for 4 h. Water and dichloromethane was added and the organic phase was passed through a phase separation filter and then evaporated to give {4-bromo-2-[(E)-ethoxycarbonylmethyliminomethyl]phenoxy}acetic acid ethyl ester, which was redissolved in dichloromethane (50 mL) and treated with NaBH(OAc)3 (2.11 g, 10 mmol) and AcOH (1 mL), and then stirred at room temperature for 5 h. Saturated Na2CO3, water and dichloromethane was added, and the organic phase was passed through a phase separation filter and evaporated to give the title compound (1.56 g, 84% overall yield).

Workup

  1. customthe organic phase was passed through a phase separation
  2. filtrationfilter
  3. customevaporated

Sources & evidence

ORD record
ord-6df38db0d98d48ecaaad85e977d81612
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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