Hydrochloric Acid → HCID 15908426, compound

HRID 428328Notes

Reaction equation

HRID 428328 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH:9]([N:12]([CH:38]([CH3:40])[CH3:39])[CH2:13][CH2:14][C@@H:15]([C:22]1[CH:27]=[C:26]([N:28]=NC2C=CC(C)=CC=2)[CH:25]=[CH:24][C:23]=1[OH:37])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:11])[CH3:10].Cl>O.C(O)C.C(OCC)C>[CH:38]([N:12]([CH:9]([CH3:11])[CH3:10])[CH2:13][CH2:14][C@@H:15]([C:22]1[CH:27]=[C:26]([NH2:28])[CH:25]=[CH:24][C:23]=1[OH:37])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:40])[CH3:39]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 24489Sodium Dithionite2×HCID 136364245HCID 136364245, compound

Product 1

HCID 15908426HCID 15908426, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of Na2S2O4 (1.23 g, 12.8 mmol) in water (10 mL) was added to a solution of (R)-N,N-diisopropyl-3-[2-hydroxy-5-(4-methylphenylazo)phenyl]-3-phenylpropanamine (0.55 g, 1.28 mmol) in ethanol (50 mL) at 75° C. during 15 min. More dry Na2S2O4 (1.23 g, 12.8 mmol) was added in 10 portions. Water was added to the solution which was then extracted with diethyl ether. The organic layer was dried (MgSO4) and evaporated to give an oil, which was chromatographed on silica (n-hexane-ethanol-triethylamine 7:3:1) to give an oil. The product was dissolved in ethanol and hydrogen chloride in diethyl ether was added. The solvent was evaporated, redissolved in water and vacuum-dried wich yielded 0.25 g (60%).

Workup

  1. extractionwas then extracted with diethyl ether
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto give an oil, which
  5. customwas chromatographed on silica (n-hexane-ethanol-triethylamine 7:3:1)
  6. customto give an oil
  7. customThe solvent was evaporated
  8. dissolutionredissolved in water
  9. customvacuum-dried wich
  10. customyielded 0.25 g (60%)

Sources & evidence

ORD record
ord-9067210b1faf4e69b9d7413185cf11bb
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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