Ethyl bromoacetate → HCID 69207180, compound

HRID 2373830Notes

Reaction equation

HRID 2373830 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[CH2:18][CH2:19][NH:20][C:21]([C:23]1[C:32]([OH:33])=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)=[O:22].[CH2:34]([O:36][C:37](=[O:40])[CH2:38]Br)C.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OC(=O)C)C>[CH3:34][O:36][C:37](=[O:40])[CH2:38][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[CH2:18][CH2:19][NH:20][C:21]([C:23]1[C:32]([OH:33])=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)=[O:22]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 11408574HCID 11408574, compound

Product 1

HCID 69207180HCID 69207180, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 3-Hydroxy-naphthalene-2-carboxylic acid [2-(4-hydroxy-4′-methanesulfonyl-biphenyl-3-yl)-ethyl]-amide (18 mg, 0.039 mmol) was in DMF were added ethylbromoacetate (0.039 mmol) and Cs2CO3 (0.039 mmol, 13 mg). The reaction mixture was for 12 hr and the reaction mixture was diluted with ethylacetate and washed with water. The organic layer was separated, dried and the crude obtained after removal of the solvent was purified on a silicagel column to afford the desired product 5 mg, and 5 mg of bis ester.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. customdried
  4. customthe crude obtained
  5. customafter removal of the solvent
  6. customwas purified on a silicagel column

Sources & evidence

ORD record
ord-f152e58a0da94624a12aa12338414eb5
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

Loading…