Ethyl bromoacetate → HCID 18367239, compound

HRID 1741422Notes

Reaction equation

HRID 1741422 reaction equation
[H-].[Na+].[C:3]1([C:9]2[N:10]=[C:11]([CH:20]([NH:22][CH:23]3[C:32]4[C:27](=[C:28]([OH:33])[CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)[CH3:21])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CN(C=O)C>[C:3]1([C:9]2[N:10]=[C:11]([CH:20]([NH:22][CH:23]3[C:32]4[C:27](=[C:28]([O:33][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)[CH3:21])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 18367330HCID 18367330, compound

Product 1

HCID 18367239HCID 18367239, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of NaH (60% oil, 66 mg) and 1-[1-(4,5-diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-hydroxynaphthalene (0.55 g) in DMF (10 ml) was stirred for 30 minutes at room temperature. To the reaction mixture was added ethyl bromoacetate (0.26 g). After being stirred for 7 hours at room temperature, the solution was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[1-(4,5-diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-ethoxycarbonylmethoxynaphthalene (0.38 g). MS (m/z): 497 (M+ +1) IR (Film): 1740 cm-1NMR (CDCl3, δ): 1.29 (3H, t, J=7.1 Hz), 1.60 (3H, t, J=6.6 Hz), 1.70-1.85 (3H, m), 1.90-2.15 (1H, m), 2.44-2.98 (2H, m), 3.89 (1H, m), 4.24-4.31 (3H, m), 4.60 (2H, s), 6.55-6.60 (1H, m), 7.08-7.11 (2H, m), 7.32-7.40 (6H, m), 7.58-7.69 (4H, m)

Workup

  1. customthe solution was partitioned between ethyl acetate and sat. NaHCO3
  2. washThe organic layer was washed with brine
  3. customThe dried solvent was evaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-21c719e9e3b34f0a872ffde90da4a561
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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