Ethyl bromoacetate → HCID 86758057, compound

HRID 1934565Notes

Reaction equation

HRID 1934565 reaction equation
[C:1]1([N:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:8](=[O:25])[O:9][CH2:10][C:11]2([OH:24])[CH2:17][CH2:16][CH2:15][C:14]3[C:18]([OH:22])=[CH:19][CH:20]=[CH:21][C:13]=3[CH:12]2[OH:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>CN(C=O)C.CCOC(C)=O>[C:26]1([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([O:9][CH2:10][C:11]2([OH:24])[CH2:17][CH2:16][CH2:15][C:14]3[C:18]([O:22][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:19][CH:20]=[CH:21][C:13]=3[CH:12]2[OH:23])=[O:25])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22467291HCID 22467291, compound

Product 1

HCID 86758057HCID 86758057, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of [(5SR,6SR)-1,5,6-trihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]methyl N,N-diphenylcarbamate (461 mg) and potassium carbonate (304 mg) in DMF (8 ml) was added ethyl bromoacetate (0.244 ml) and stirred at room temperature for 18 hours. The reaction mixture was diluted with EtOAc, washed with water and then brine. It was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 4:5) to give ethyl {[(5SR,6SR)-6-(N,N-diphenylcarbamoyloxy)methyl-5,6-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-1 -yl]oxy}acetate (459.6 mg) as an amorphous solid.

Workup

  1. washwashed with water
  2. dry with materialIt was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 4:5)

Sources & evidence

ORD record
ord-16c9e7f46087419081ec71afe18701b7
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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