Ethyl bromoacetate → HCID 58646722, compound

HRID 901988Notes

Reaction equation

HRID 901988 reaction equation
[CH2:1]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[OH:19])[CH2:11][C@H:10]1[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CS(C)=O>[CH2:1]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:19][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:11][C@H:10]1[OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10942334Sodium MethoxideHCID 58646734HCID 58646734, compound

Product 1

HCID 58646722HCID 58646722, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring solution of trans 3-benzylamino-2,5-dihydroxy-1,2,3,4-tetrahydronaphthalene (14 g) in dry dimethylsulfoxide (150 mL) was added sodium methoxide (3.05 g). This was stirred for 10 min at room temperature, then cooled in a 10° C. bath while ethyl bromoacetate (9.1 g) was added over 3 min, during which the temperature of the mixture remained below 25° C. The cooling bath was removed, and the reaction mixture was stirred for 4.5 h at room temperature under nitrogen. Dilution with a half-saturated aqueous sodium bicarbonate solution (800 mL) was followed by extraction with diethyl ether (250 mL four times). The combined extracts were washed sequentially with cold 5% aqueous sodium hydroxide solution, water (300 mL twice), and brine and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum to provide crude product. The crude product was recrystallized from 50% ethyl acetate in hexane (100 mL) to yield the title product (13 g) as a white solid (mp 93-97° C.).

Workup

  1. additionwas added over 3 min, during which the temperature of the mixture
  2. customremained below 25° C
  3. customThe cooling bath was removed
  4. stirringthe reaction mixture was stirred for 4.5 h at room temperature under nitrogen
  5. extractionDilution with a half-saturated aqueous sodium bicarbonate solution (800 mL) was followed by extraction with diethyl ether (250 mL four times)
  6. washThe combined extracts were washed sequentially with cold 5% aqueous sodium hydroxide solution, water (300 mL twice), and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under vacuum
  9. customto provide crude product
  10. customThe crude product was recrystallized from 50% ethyl acetate in hexane (100 mL)

Sources & evidence

ORD record
ord-134a6f8361e740e59e177be09a4c3555
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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