Sodium hydride → HCID 86638389, compound

HRID 1096240Notes

Reaction equation

HRID 1096240 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrC[CH2:18][CH2:19][C:20]([N:22]([O:24][CH3:25])[CH3:23])=[O:21].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:18][CH2:19][C:20](=[O:21])[N:22]([O:24][CH3:25])[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14642623130250-57-6HCID 226177365-Oxo-(1,4)diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 86638389HCID 86638389, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester 5.9 g (28 mmol) and 4-bromo-N-methoxy-N-methyl-butyramide 5.4 g (28 mmol) in DMF (220 ml) was added NaH 1.3 g (30 mmol, 55% dispersion in oil), the mixture allowed to reach RT and the mixture stirred for a further 2 h. The reaction was then concentrated, the residue redissolved in EtOAc and washed with 10% aq. KHSO4 solution, brine, dried (MgSO4) and concentrated affording the title compound 9.1 g (quant) as white foam. MS: 330.3 (MH+).

Workup

  1. customto reach RT
  2. concentrationThe reaction was then concentrated
  3. dissolutionthe residue redissolved in EtOAc
  4. washwashed with 10% aq. KHSO4 solution, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-50f2f34f84034f4090c72a297f659ff2
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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