Tetrahydrofuran → Sodium (5-(((benzyloxy)carbonyl)amino)pyridin-2-yl)acetate

HRID 714913Notes

Reaction equation

HRID 714913 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[CH:8][N:7]=1)C.O1CCCC1.[OH-].[Na+:30]>CC(O)C>[CH2:16]([O:15][C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([O-:23])=[O:3])=[N:7][CH:8]=1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na+:30]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 131734078Benzyl 6-((ethoxycarbonyl)methyl)pyridin-3-ylcarbamate

Product 1

HCID 131734079Sodium (5-(((benzyloxy)carbonyl)amino)pyridin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of ethyl(5-(((benzyloxy)carbonyl)amino)pyridin-2-yl)acetate (1.0 g) obtained in Step A of Example 363 in a mixed solvent of tetrahydrofuran (20 mL) and 2-propanol (5.0 mL) was added 2 M aqueous sodium hydroxide solution (6.4 mL) in an ice bath, and the mixture was stirred at the same temperature for 3 hr. The reaction mixture was collected by filtration to give the title compound (2.6 g).

Workup

  1. filtrationThe reaction mixture was collected by filtration

Sources & evidence

ORD record
ord-42dd20940f684279997c62dea8585c8d
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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