Sodium hydride → HCID 59003218, compound

HRID 2353943Notes

Reaction equation

HRID 2353943 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:11][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13].[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[N:11]([CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:12]([O:14][CH:15]([CH3:16])[CH3:17])=[O:13]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 590031022-Isopropoxycarbonylamino-6-methyl-benzoic acid methyl ester

Product 1

HCID 59003218HCID 59003218, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Add a solution of 2-isopropoxycarbonylamino-6-methyl-benzoic acid methyl ester (3.77 g, 15.0 mmol) in DMF (60 mL) to a suspension of sodium hydride 60% dispersion mineral oil (600 mg, 15.0 mmol) in DMF (60 mL) at 0° C. under an atmosphere of nitrogen and allow to reach room temperature over 1 h. Add ethyl 4-bromobutyrate (3.2 mL, 22 mmol) and stir at room temperature for 14 h. Dilute with ethyl acetate, wash with 1M HCl, water and brine. Dry the organic layer over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to provide the title compound (4.60 mg, 84%): 1H NMR (CDCl3, 300 MHz) δ 1.05-1.30 (m, 9H), 1.90 (m, 2H), 2.32 (m, 2H), 2.36 (s, 3H), 3.85 (s, 3H), 4.11 (q, J=7.3 Hz, 2H), 4.88 (m, 1H), 7.02 (m, 1H), 7.16 (d, J=7.7 Hz, 1H), 7.31 (t, J=7.9 Hz, 1H). MS (ES+): 366 (M+H).

Workup

  1. washwash with 1M HCl, water and brine
  2. dry with materialDry the organic layer over anhydrous sodium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure
  5. customPurify the residue by flash chromatography
  6. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-dcf8b31138e34c499eba96fde29a39ca
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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