Ethyl Acetate → HCID 18974058, compound

HRID 2395010Notes

Reaction equation

HRID 2395010 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][CH2:17][CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]([NH2:39])=[O:38].C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:36][C:37](=[O:38])[NH2:39])=[CH:11][C:10]=1[CH2:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 18973718HCID 18973718, compound

Product 1

HCID 18974058HCID 18974058, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 4-[3-(2-benzyloxy-5-hydroxyphenyl)propyl]benzoate (510 mg) and potassium carbonate in DMF (10 ml) was added bromoacetamide (384 mg). The reaction was stirred for 48 hours, poured into ethyl acetate (50 ml), washed with 1M HCl (50 ml) and brine (50 ml), dried (magnesium sulphate) filtered and evaporated. The residue was purified by subjecting to chromatography on silica gel using ethyl acetate:hexane (75:25) as eluant. There was thus obtained methyl 4-[3-(2-benzyloxy-5-(carbamoylmethoxy)phenyl)propyl]benzoate (200 mg).

Workup

  1. washwashed with 1M HCl (50 ml) and brine (50 ml)
  2. dry with materialdried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-13ebfb78f42840adadc0ae995e599db4
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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