Hydrochloric Acid → HCID 131718848, compound

HRID 2260399Notes

Reaction equation

HRID 2260399 reaction equation
[Na].[CH:2]1C2C(=CC=CC=2)C=CC=1.C1(S([NH:21][C@@H:22]2[CH2:26][CH2:25][CH2:24][C@H:23]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:30][CH:29]=2)(=O)=O)C=CC=CC=1.Cl>COCCOC.O>[NH2:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][C:35]([O:37][CH2:38][CH3:2])=[O:36])=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 931NaphthaleneHCID 5360545SodiumHCID 53661584HCID 53661584, compound

Product 1

HCID 131718848HCID 131718848, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

0.5 g (21 mmoles) of sodium is added to a mixture of 2.6 g (21 mmoles) of naphthalene and 20 ml of 1,2-dimethoxyethane, under a flow of nitrogen. After stirring 1 hour at 20° C., a solution of 2 g (5.2 mmoles) of methyl trans-4-[[2-[[(phenyl)sulfonyl]amino]cyclopentyl]methyl]benzeneacetate in 20 ml of 1,2-dimethoxyethane is added dropwise during 1 hour, at room temperature. After stirring 1 hour at 20° C., 40 ml of water are added dropwise, before washing with ethyl acetate. The aqueous phase acidified with diluted HCl is washed with ethyl acetate, before being concentrated to dryness under reduced pressure. The residue is captured by 50 ml of absolute ethanol and the white suspension obtained is saturated at 0° C. with gaseous HCl. After stirring 16 h at 20° C., the reaction mixture is concentrated under reduced pressure, captured with H2O, made basic with NH4OH and extracted with ethyl acetate. This organic phase after washing with H2O saturated with NaCl is dried over Na2SO4, concentrated, to give 0.5 g (yield=39.3%) of a partially crystallized brown oil, which is used without any other purification.

Workup

  1. stirringAfter stirring 1 hour at 20° C.
  2. washbefore washing with ethyl acetate
  3. washis washed with ethyl acetate
  4. concentrationbefore being concentrated to dryness under reduced pressure
  5. customthe white suspension obtained
  6. stirringAfter stirring 16 h at 20° C.
  7. concentrationthe reaction mixture is concentrated under reduced pressure
  8. extractionextracted with ethyl acetate
  9. washThis organic phase after washing with H2O saturated with NaCl
  10. dry with materialis dried over Na2SO4
  11. concentrationconcentrated
  12. customto give 0.5 g (yield=39.3%) of a partially crystallized brown oil, which
  13. customis used without any other purification

Sources & evidence

ORD record
ord-1853dade27fc4557bf6d4fff1ecf8397
Source dataset
uspto-grants-1995_12
Patent number
US05476846

Reaction notes

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