Cesium carbonate → HCID 53809809, compound

HRID 367328Notes

Reaction equation

HRID 367328 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][C:16]([OH:22])=[CH:17][CH:18]=2)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26])=[CH:17][CH:18]=2)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2255442-Bromo-N,N-dimethylacetamideHCID 54163446HCID 54163446, compound

Product 1

HCID 53809809HCID 53809809, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2-(Benzyloxycarbonylamino)-7-hydroxytetralin (13.4 g) was dissolved in 120 ml of N,N-dimethylformamide, 8.27 g of 2-bromo-N,N-dimethylacetamide and 22.0 g of cesium carbonate were added to the solution, and the mixture was stirred at room temperature for 6 hours. The reaction solution was poured into ice-water, the 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 resulting residue was crystallized by adding diethyl ether to give 14.0 g of (S)-2-[2-(benzyloxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide having a melting point of 117 to 118° C.

Workup

  1. extractionthe 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 resulting residue was crystallized
  6. additionby adding diethyl ether

Sources & evidence

ORD record
ord-675fb3083e8640f0aa3e6bf086901caf
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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