Tetrahydrofuran → 2-{3-[(1R,2R)-2-Carboxy-1-(2-chlorobenzyl)-2-hydroxy-ethylcarbamoyl]-propyl}-benzoic Acid

HRID 2361113Notes

Reaction equation

HRID 2361113 reaction equation
C([O:5][C:6]([C@H:8]([OH:33])[C@H:9]([NH:18][C:19]([CH2:21][CH2:22][CH2:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=[O:27])=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=[O:7])CCC.C1COCC1.[OH-].[Na+]>CC(O)=O>[C:6]([C@H:8]([OH:33])[C@H:9]([NH:18][C:19]([CH2:21][CH2:22][CH2:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=[O:27])=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 710736552-{3-[(1R,2R)-2-butoxycarbonyl-1-(2-chloro-benzyl)-2-hydroxy-ethylcarbamoyl]-propyl}-benzoic acid

Product 1

HCID 710735762-{3-[(1R,2R)-2-Carboxy-1-(2-chlorobenzyl)-2-hydroxy-ethylcarbamoyl]-propyl}-benzoic AcidYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-{3-[(1R,2R)-2-Butoxycarbonyl-1-(2-chloro-benzyl)-2-hydroxy-ethylcarbamoyl]-propyl}-benzoic acid (110 mg, 230 μmol, 1.0 eq.) was combined with THF (2.1 mL), and 1 M aqueous NaOH (480 μL, 2.0 eq.). The mixture was stirred at room temperature for 1 hour. Upon completion of the reaction was completed, AcOH (1 mL) was added and the product was purified by preparative HPLC. The clean fractions were combined and lyophilized to yield the title compound (95 mg, 99% purity). MS m/z [M+H]+ calc'd for C21H22ClNO6, 420.11. found 420.

Workup

  1. customthe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-11ed2239850b4fdb98def45eac17ed8b
Source dataset
uspto-grants-2014_04
Patent number
US08686184B2

Reaction notes

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