Sodium hydride → HCID 18319530, compound

HRID 1699384Notes

Reaction equation

HRID 1699384 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[C:18]2[O:17][CH2:16][CH2:15][C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:6].[H-].[Na+]>CN(C)C=O>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[C:18]2[O:17][CH2:16][CH2:15][C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18319605HCID 18319605, compound

Product 1

HCID 18319530HCID 18319530, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 9-(4-chloro-1-oxobutylamino)-2,3-dihydro-1-benzoxepin-4-carboxylate (0.44 g) in N,N-dimethylformamide (4.4 ml) was added sodium hydride (0.17 g, 60%) at ambient temperature. The reaction mixture was stirred for 1.5 hours at the same temperature and partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by medium pressure liquid chromatography (silica gel) using a mixture of ethyl acetate and n-hexane (1:4˜1:1) to give a solid of ethyl 2,3-dihydro-9-(2-oxo-1-pyrrolidinyl)-1-benzoxepin-4-carboxylate (0.21 g).

Workup

  1. custompartitioned between ethyl acetate and 1N hydrochloric acid
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by medium pressure liquid chromatography (silica gel)
  6. additiona mixture of ethyl acetate and n-hexane (1:4˜1:1)

Sources & evidence

ORD record
ord-ba07131fd42347abb6411a432efa4a4c
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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