Sulfuric Acid → HCID 69507129, compound

HRID 1296241Notes

Reaction equation

HRID 1296241 reaction equation
CO[CH:3]([O:18]C)[CH2:4][NH:5][CH2:6][CH2:7][NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1O.OS(O)(=O)=O>C(Cl)(Cl)Cl>[CH2:4]1[CH:3]2[N:8]([C:9](=[O:17])[C:10]3[C:11]([O:18]2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:7][CH2:6][NH:5]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 68689040HCID 68689040, compound

Product 1

HCID 69507129HCID 69507129, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of N-[2-(2,2-dimethoxy-ethylamino)-ethyl]-2-hydroxy benzamide (300 mg, 1.11 mmol) in CHCl3 (100 mL) was added conc H2SO4 (2 mL). The reaction was refuxed overnight, then cooled to room temperature then poured into a mixture of ice-saturated NaHCO3 solution. The mixture was extracted with EtOAc (3×50 mL). The organic layers were combined, washed with brine, dried on MgSO4, and conc in vacuo to yield a yellowish oil. The oil was then purified by chiral HPLC using an OD column with 10% iPrOH in heptane to yield 50 mg of the R enantiomer as white solid, MS (ESI) 205 (M+H), and 56 mg of the S enantiomer as white solid, MS (ESI) 205 (M+H).

Workup

  1. additionthen poured into a mixture of ice-saturated NaHCO3 solution
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. washwashed with brine
  4. customdried on MgSO4
  5. customconc in vacuo to yield a yellowish oil
  6. customThe oil was then purified by chiral HPLC
  7. customto yield 50 mg of the R enantiomer as white solid, MS (ESI) 205 (M+H), and 56 mg of the S enantiomer as white solid, MS (ESI) 205 (M+H)

Sources & evidence

ORD record
ord-928ea150e21d40e59c6957174173e359
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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