Triethylamine → HCID 10449402, compound

HRID 1614757Notes

Reaction equation

HRID 1614757 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, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3.6 g of (R)-3-chloromandelic acid, 3.5 g of S(-)-2-amino-7-hydroxy-1,2,3,4-tetrahydronaphtalene monohydrate (PREPARATION III) and 7.7 g of BOP in 60 ml of anhydrous methylene chloride under nitrogen stream, there is added 2.7 ml of triethylamine. The solution obtained is stirred for 5 hours at room temperature, then 400 ml of ethyl acetate are added thereto and the organic phase is washed with water, separated and evaporated to dryness. The residue thus obtained is treated with 150 ml of N sodium hydroxide and extracted with ethyl ether. The organic phase is eliminated. The aqueous phase is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase thus obtained is washed with water, dried over sodium sulfate, filtered and evaporated to dryness. The oil thus obtained is purified by flash chromatography (elution with a 70/30 mixture of ethyl acetate/cyclohexane). An amount of 4 g (63%) of N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(R)-3-chloromandelamide is obtained as a very thick whittish oil that is treated with petroleum ether; a solid having an undefined melting point is obtained; [alpha]=-95° (methanol, c= 1%). This product is identical with the compound SR 58587 of Example 9(b), the (S, R) configuration of which is thus confirmed.

Workup

  1. customThe solution obtained
  2. washthe organic phase is washed with water
  3. customseparated
  4. customevaporated to dryness
  5. customThe residue thus obtained
  6. extractionextracted with ethyl ether
  7. extractionextracted with ethyl acetate
  8. customThe organic phase thus obtained
  9. washis 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. washelution
  16. additionwith a 70/30 mixture of ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-f820f7723ba2431faae7a7175c12e66b
Source dataset
uspto-grants-1993_03
Patent number
US05198586

Reaction notes

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