Glycine ethyl ester, hydrochloride → HCID 69599109, compound

HRID 1823957Notes

Reaction equation

HRID 1823957 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[O:12][C:13](=[O:31])/[C:14](=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Br:30])=[CH:19][CH:18]=2)/[N:15]=1)(=O)C.Cl.[CH2:33]([O:35][C:36](=[O:39])[CH2:37][NH2:38])[CH3:34]>C(Cl)Cl>[Br:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[O:23][C:20]1[CH:21]=[CH:22][C:17](/[CH:16]=[C:14](\[NH:15][C:11](=[O:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[OH:4])/[C:13]([NH:38][CH2:37][C:36]([O:35][CH2:33][CH3:34])=[O:39])=[O:31])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 69599200HCID 69599200, compound

Product 1

HCID 69599109HCID 69599109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A portion of 2-{(4Z)-4-[4-(2-bromophenoxy)benzylidene]-5-oxo-4,5-dihydro-1,3-oxazol-2-yl}phenyl acetate (0.10 g, 0.229 mmol), prepared as described above, is suspended in DCM (10 mL) and treated with glycine ethyl ester hydrochloride (67 m g, 0.48 mmol). The reaction is heated to 60° C. for 4 hours and then concentrated. The resulting solid is triturated with EtOAc to provide ethyl N-{(2Z)-3-[4-(2-bromophenoxy)phenyl]-2-[(2-hydroxybenzoyl)amino]prop-2-enoyl}glycinate, which is subsequently suspended in 1N NaOH (1 mL) and ethanol (1 mL) and stirred at 25° C. for 3 hours. The ethanol is removed and several drops of concentrated HCl added and a precipitate is formed. Filtration afforded 65 mg of N-{(2Z)-3-[4-(2-bromophenoxy)phenyl]-2-[(2-hydroxybenzoyl)amino]prop-2-enoyl}glycine.

Workup

  1. concentrationconcentrated
  2. customThe resulting solid is triturated with EtOAc

Sources & evidence

ORD record
ord-fa5102c26e0e40d59d2e0c6dd6cf60d7
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

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