Ethyl bromoacetate → HCID 59785896, compound

HRID 1673206Notes

Reaction equation

HRID 1673206 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([OH:26])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([O:26][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25061041HCID 25061041, compound

Product 1

HCID 59785896HCID 59785896, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

To the product of Example 68 (250 mg, 0.575 mmol) was added NaH (73.6 mg, 1.84 mmol, 60%) and ethyl 2-bromoacetate (0.23 mL 2.07 mmol) in DMF (3 mL). The reaction was stirred 3 h at 30° C. and 15 h at rt. The reaction was diluted with EtOAc and washed with 2 M aq HCl and brine. The concentrated residue was purified by flash chromatography on silica gel gradient eluted with 0-33% EtOAc in hexane affording the title compound. (LC-2) HPLC/MS: 520.1 (M+1), 522.0 (M+3); Rt=4.43 min.

Workup

  1. washwashed with 2 M aq HCl and brine
  2. customThe concentrated residue was purified by flash chromatography on silica gel gradient
  3. washeluted with 0-33% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-96dcba26a4fd49c7a46a7efacf195720
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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