Water → HCID 53730197, compound

HRID 367326Notes

Reaction equation

HRID 367326 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-].[Cs+].[Cs+].Br[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].O>CN(C)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][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrateHCID 10244501HCID 10244501, compound

Product 1

HCID 53730197HCID 53730197, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2-(tert-Butoxycarbonylamino)-7-hydroxytetralin (400 mg) was dissolved in 8 ml of N,N-dimethylformamide, 3.16 g of cesium carbonate and 650 μl of ethyl 4-bromobutyrate were added to the solution, and the mixture was stirred at room temperature for 1.5 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, and the extract was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel medium pressure liquid column chromatography (eluent: hexane/ethyl acetate=1/1) to give 488 mg of ethyl (S)-4-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yloxy]butyrate having a meltin(point of 96 to 98° C.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel medium pressure liquid column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-829c292b5d384c4d819c94b24108195d
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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