Sodium Hydroxide → HCID 67663431, compound

HRID 1957346Notes

Reaction equation

[CH2:1]([N:4]([CH:21]1[CH:24]([C:25]([O-:27])=[O:26])[CH:23]([C:28]([O-:30])=[O:29])[CH2:22]1)[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=[O:6])[CH2:2][CH3:3].[OH-].[Na+]>>[CH2:1]([N:4]([CH:21]1[CH:24]([C:25]([OH:27])=[O:26])[CH:23]([C:28]([OH:30])=[O:29])[CH2:22]1)[C:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)=[O:6])[CH2:2][CH3:3]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 131720772HCID 131720772, compound

Product 1

HCID 67663431HCID 67663431, compound

Procedure

The compound resulting from Example 124A is reacted with propionyl chloride in the presence of triethylamine to give methyl 1,2-di(propionylamino)cyclobutane-3,4-dicarboxylate. Reduction of the diamide with borane-tetrahydrofuran complex at 0° C. affords methyl 1,2-di(n-propylamino)cyclobutane-3,4-dicarboxylate. Treatment of this secondary amine with the acid chloride of 4-phenoxyphenylacetic acid in the presence of triethylamine yields methyl1,2-di[(N-propyl-N-(4-phenoxybenzyl)carbonylamino]cyclobutane-3,4-dicarboxylate. Hydrolysis of the methyl esters with aqueous sodium hydroxide affords the title compound.

Sources & evidence

ORD record: ord-911f553b5476499b89aaed776d92a876
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783593

Reaction notes

Loading…