Hydrochloric Acid → (4'-Amino-2'-[(benzyloxycarbonyl-ethyl-amino)-methyl]-6-methoxy-biphenyl-3-yl)-acetic acid ethyl ester

HRID 2197332Notes

Reaction equation

HRID 2197332 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=2[CH2:23][N:24]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:25][CH3:26])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].[Sn](Cl)Cl.Cl>CCO.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:37])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=2[CH2:23][N:24]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:25][CH3:26])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 58149106{2'-[(Benzyloxycarbonyl-ethyl-amino)-methyl]-6-methoxy-4'-nitro-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 58148932(4'-Amino-2'-[(benzyloxycarbonyl-ethyl-amino)-methyl]-6-methoxy-biphenyl-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {2′-[(benzyloxycarbonyl-ethyl-amino)-methyl]-6-methoxy-4′-nitro-biphenyl-3-yl}-acetic acid ethyl ester (0.70 g, 1.75 mmol) in EtOH (70 mL) was added tin (II) chloride (1.97 g, 8.75 mmol). The reaction was heated to reflux for 5 h, and then the mixture was acidified to pH 1 with concentrated HCl and diluted with EtOAc. The resulting biphasic mixture was filtered through Celite, and the organic layer was separated. The aqueous layer was neutralized to pH 7 with solid NaOH and extracted with EtOAc. The combined organic extracts were dried and filtered, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 h
  3. filtrationThe resulting biphasic mixture was filtered through Celite
  4. customthe organic layer was separated
  5. extractionextracted with EtOAc
  6. customThe combined organic extracts were dried
  7. filtrationfiltered
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0ebddbd369ca4b34b763b140a4fd8c92
Source dataset
uspto-grants-2012_12
Patent number
US08338484B2

Reaction notes

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