Water → HCID 53730197, compound

HRID 1003273Notes

Reaction equation

HRID 1003273 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 N,N-dimethylformamide (8 ml), and cesium carbonate (3.16 g) and ethyl 4-bromobutyrate (650 μl) were added to the solution at room temperature with stirring. After reaction for 1.5 hours, water was poured into the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1) gave ethyl (S)-4-[2-(tert-butoxycarbonyl-amino)-1,2,3,4-tetrahydronaphthalen-7-yloxy]butyrate (488 mg) having a melting point of 96-98° C.

Workup

  1. customAfter reaction for 1.5 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-72c8c77aa57c4b96baf25690dc450639
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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