Ethyl bromoacetate → HCID 10427900, compound

HRID 1590360Notes

Reaction equation

HRID 1590360 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10264739HCID 10264739, compound

Product 1

HCID 10427900HCID 10427900, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 10.8 g of (R)-2-tert-butoxycarbonylamino-7-hydroxytetraline (a) in 300 ml of acetone, is heated at reflux under stirring for 6 hours in the presence of 12.4 g of powdered anhydrous potassium carbonate and 15.1 g of ethyl bromoacetate. After filtration, acetone is evaporated under reduce pressure and the residue is taken up with ethyl ether. The solution so obtained is washed with water, dried over sodium sulfate and evaporated to dryness. The residue is taken up with ethyl ether and crystallized from isopropyl ether. Thus, 4.8 g of (R)-2-tert-butoxycarbonylamino-7-carbethoxymethoxytetraline are obtained; m.p. 113°-115° C., /alpha/=+57.97° (methanol, c=1%).

Workup

  1. temperatureat reflux
  2. filtrationAfter filtration, acetone
  3. customis evaporated
  4. customThe solution so obtained
  5. washis washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-8613c22d289040e0a8a1ea6322ef87e7
Source dataset
uspto-grants-1993_04
Patent number
US05202466

Reaction notes

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