Mandelic Acid → HCID 53752892, compound

HRID 1614754Notes

Reaction equation

HRID 1614754 reaction equation
[C:1]([OH:11])(=O)[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].F[P-](F)(F)(F)(F)F.[N:19]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2N=N1.[CH2:39](N(CC)CC)[CH3:40].[Cl-].[Na+].C([O:51][CH2:52][CH3:53])(=O)C>C(Cl)Cl>[OH:51][C:52]1[CH:53]=[C:25]2[C:26]([CH2:27][CH2:22][C@@H:23]([NH:19][C:1](=[O:11])[CH:2]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[OH:3])[CH2:24]2)=[CH:40][CH:39]=1

Participants

7

Reactant 5

HCID 1292Mandelic AcidHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 53752892HCID 53752892, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.0 g of R(+)-2-amino-7-hydroxy-1,2,3,4-tetrahydronaphtalene monohydrate (PREPARATION II), 5.8 g of racemic mandelic acid, 15.3 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 for 30 minutes at room temperature 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)-mandelamide as diastereoisomeric mixture.

Workup

  1. customthe solution thus obtained
  2. stirringThe mixture is stirred for 30 minutes at room temperature
  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-54835b776429407c8a97f0719a43cfb6
Source dataset
uspto-grants-1993_03
Patent number
US05198586

Reaction notes

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