Triethylamine → HCID 10449402, compound

HRID 2248986Notes

Reaction equation

HRID 2248986 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C@@H: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].[OH-].[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])[C@@H: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 8471TriethylamineHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

Product 1

HCID 10449402HCID 10449402, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 3.6 g of (R)-3-chloromandelic acid (Bull. Soc. Chim. Fr., 1973, 12, 3330) is reacted with 3.5 g of S(-)-2-amino-7-hydroxytetralin monohydrate (PREPARATION IV) and 7.7 g of BOP in 60 ml of anhydrous methylene chloride under nitrogen stream. An amount of 2.7 ml of triethylamine is added, the solution thus obtained is left under stirring for 5 hours at room temperature, then 400 ml of ethyl acetate are added thereto. After washing with a sodium bicarbonate solution, then with water, then with hydrochloric acid and finally with water, the organic phase is separated and evaporated to dryness. The residue thus obtained is treated with 150 ml of N sodium hydroxide and extracted with ethyl ether that is then eliminated. The aqueous phase is made acid with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate, filtered and evaporated to dryness. The oil thus obtained is purified by flash chromatography by eluting with a 70/30 mixture of ethyl acetate/ cyclohexane. The N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(R)-3-chloromandelamide, is obtained as a very thick whitish oil that is treated with petroleum ether to give a solid having an indefinite melting point, SR 58587, |alpha|=-95° (methanol, c=1%).

Workup

  1. customthe solution thus obtained
  2. waitis left
  3. washAfter washing with a sodium bicarbonate solution
  4. customwith water, then with hydrochloric acid and finally with water, the organic phase is separated
  5. customevaporated to dryness
  6. customThe residue thus obtained
  7. extractionextracted with ethyl ether that
  8. extractionextracted with ethyl acetate
  9. washThe organic phase is washed with water
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. customevaporated to dryness
  13. customThe oil thus obtained
  14. customis purified by flash chromatography
  15. washby eluting with a 70/30 mixture of ethyl acetate/ cyclohexane

Sources & evidence

ORD record
ord-5af060cfdadf40bd8c20462c130adc09
Source dataset
uspto-grants-1991_08
Patent number
US05041606

Reaction notes

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