Sodium Chloride → HCID 11014455, compound

HRID 1590364Notes

Reaction equation

HRID 1590364 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][CH:9]=2)[CH2:4]1.[C:20](O)(=[O:29])[C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[OH:22].C(N(CC)CC)C.[Cl-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:15]([CH2:14][O:13][C:7]1[CH:6]=[C:5]2[C:10]([CH2:11][CH2:12][C@H:3]([NH:2][C:20](=[O:29])[C@@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[OH:22])[CH2:4]2)=[CH:9][CH:8]=1)([O:17][CH2:18][CH3:19])=[O:16]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 11914(-)-Mandelic acidHCID 18648615HCID 18648615, compound

Product 1

HCID 11014455HCID 11014455, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5.7 g of (S)-2-amino-7-carbethoxymethoxytetraline hydrochloride, 3 g of (R)-mandelic acid and 8 g of benzotriazolyl-N-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) in 100 ml of anhydrous methylene chloride, there is slowly added 5.6 ml of triethylamine, then the solution thus obtained is left under stirring at room temperature for 5 hours. After addition of 150 ml of a saturated solution of sodium chloride, the mixture is left under stirring for 30 minutes at room temperature, added with 500 ml of ethyl acetate. The organic phase is washed at first with a 1N solution of hydrochloric acid, then with a saturated solution of sodium bicarbonate and sodium chloride. The organic solution is dried on sodium sulfate, filtered and evaporated to dryness. The oil thus obtained is purified by flash chromatography by using a mixture of ethyl acetate/cyclohexane 55/45 as a solvent. The resulting solid is triturated in 20 ml of ethyl ether and the product thus obtained is crystallized from ethyl acetate to give N-[(2S)-7-carbethoxymethoxy-1,2,3,4 -tetrahydronaphth-2-yl]-(R)-mandelamide; m.p. 115°-117° C.; /alpha/=-98.3° (methanol, c=1%). Yield: 55%.

Workup

  1. customthe solution thus obtained
  2. waitis left
  3. waitthe mixture is left
  4. stirringunder stirring for 30 minutes at room temperature
  5. washThe organic phase is washed at first with a 1N solution of hydrochloric acid
  6. customThe organic solution is dried on sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe oil thus obtained
  10. customis purified by flash chromatography
  11. additiona mixture of ethyl acetate/cyclohexane 55/45 as a solvent
  12. customThe resulting solid is triturated in 20 ml of ethyl ether
  13. customthe product thus obtained
  14. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c4cf77efc73b42c2b97d6974b42b5d45
Source dataset
uspto-grants-1993_04
Patent number
US05202466

Reaction notes

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