Sodium Chloride → N-[(2R)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(RS)-3-chloromandelamide

HRID 1614753Notes

Reaction equation

HRID 1614753 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]([OH:9])[C:6]([OH:8])=O.F[P-](F)(F)(F)(F)F.[N:20]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2N=N1.[CH2:40](N(CC)CC)[CH3:41].[Cl-].[Na+].C([O:52][CH2:53][CH3:54])(=O)C>C(Cl)Cl>[OH:52][C:53]1[CH:54]=[C:26]2[C:27]([CH2:28][CH2:23][C@@H:24]([NH:20][C:6](=[O:8])[CH:5]([C:4]3[CH:10]=[CH:11][CH:12]=[C:2]([Cl:1])[CH:3]=3)[OH:9])[CH2:25]2)=[CH:41][CH:40]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 859813-Chloromandelic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 18650807N-[(2R)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(RS)-3-chloromandelamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7 g of R(+)-2-amino-7-hydroxy-1,2,3,4-tetrahydronaphtalene monohydrate (PREPARATION II), 7.2 g of racemic 3-chloromandelic acid, 16 g of BOP in 200 ml of anhydrous methylene chloride, there is added 3.9 g of triethylamine slowly and the solution thus obtained is stirred at room temperature for 3 hours. A volume of 100 ml of a saturated sodium chloride solution is added. The mixture is stirred at room temperature for 30 minutes and 400 ml of ethyl acetate are added thereto. The phases thus obtained are separated and the aqueous phase is eliminated. The organic phase is washed twice with 50 ml of 2N hydrochloric acid, then twice with a saturated sodium bicarbonate solution and, then, the organic phase is dried over sodium sulfate, filtered and evaporated to dryness. The product thus obtained is purified by flash chromatography (elution with a 6/4 mixture of ethyl acetate/cyclohexane) and all of the fractions are collected to give the N-[(2R)-7-hydroxy-1,2,3,4-tetrahydronaphth-2 -yl]-(RS)-3-chloromandelamide as diastereoisomeric mixture.

Workup

  1. customthe solution thus obtained
  2. stirringThe mixture is stirred at room temperature for 30 minutes
  3. customThe phases thus obtained
  4. customare separated
  5. washThe organic phase is washed twice with 50 ml of 2N hydrochloric acid
  6. dry with materialtwice with a saturated sodium bicarbonate solution and, then, the organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe product thus obtained
  10. customis purified by flash chromatography (
  11. washelution
  12. additionwith a 6/4 mixture of ethyl acetate/cyclohexane) and all of the fractions
  13. customare collected

Sources & evidence

ORD record
ord-401b8002929a413fae72697162055378
Source dataset
uspto-grants-1993_03
Patent number
US05198586

Reaction notes

Loading…