Tetrahydrofuran → 2-[3-((1R,2R)-1-Benzyl-2-carboxy-2-hydroxy-ethylcarbamoyl)-propyl]-benzoic Acid

HRID 2361124Notes

Reaction equation

HRID 2361124 reaction equation
[CH2:1]([C@@H:8]([NH:16][C:17]([CH2:19][CH2:20][CH2:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25])=[O:18])[C@H:9]([C:11]([O:13]CC)=[O:12])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+]>CC(O)=O>[CH2:1]([C@@H:8]([NH:16][C:17]([CH2:19][CH2:20][CH2:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25])=[O:18])[C@H:9]([C:11]([OH:13])=[O:12])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 710738542-[3-((1R,2R)-1-benzyl-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-propyl]-benzoic acid

Product 1

HCID 710737182-[3-((1R,2R)-1-Benzyl-2-carboxy-2-hydroxy-ethylcarbamoyl)-propyl]-benzoic AcidYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Two thirds of the crude 2-[3-((1R,2R)-1-benzyl-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-propyl]-benzoic acid for the previous example, was combined with THF (8 mL) and 10 M aqueous NaOH (134 μL, 4.0 eq.). The reaction was stirred for 4 hours. Upon completion of the reaction was completed, AcOH (1.5 mL) was added and the product was purified by preparative HPLC to yield the title compound (50 mg, 95% purity). MS m/z [M+H]+ calc'd for C21H23NO6, 386.15. found 386.2.

Workup

  1. customthe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-8f8296ff8add46e0b2fba83815eba337
Source dataset
uspto-grants-2014_04
Patent number
US08686184B2

Reaction notes

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