Water → HCID 67385631, compound

HRID 905968Notes

Reaction equation

HRID 905968 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:12](=[O:13])[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].[CH3:23]I.O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([CH3:23])[C:12](=[O:13])[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:14]([N:9]1[CH2:8][CH2:7][CH:6]([CH3:4])[C:12](=[O:13])[CH2:11][CH2:10]1)(=[O:16])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate

Product 2

HCID 59363368HCID 59363368, compoundYield 95%HCID 67385631HCID 67385631, compoundYield 190.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of compound racemic 5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (2.5 g, 8.77 mmole) in 10 mL of DMF was added at 0° C. to a stirred suspension of NaH 60% dispersion in oil (355 mg, 8.77 mmole) in 10 mL of DMF. The reaction mixture was allowed to stir RT for one hour before being cooled to 0° C. Methyl iodide (1.37 mL, 21.92 mmole, 2.5 eqv) was added slowly and the reaction mixture was stirred at RT for 3 h before being poured into cold H2O and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried, and evaporated to give 2.5 g of 4-methyl-5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester desired compound (95% yield).

Workup

  1. temperaturebefore being cooled to 0° C
  2. stirringthe reaction mixture was stirred at RT for 3 h
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic layer was washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-f06f018167b34ea2aa5c4c2ab3fc29b9
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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