Acetic Acid → HCID 19434001, compound

HRID 1735998Notes

Reaction equation

HRID 1735998 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([Cl:9])[S:6][C:5]=1[S:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:12])=[O:11])(=[O:3])[CH3:2].Br.C(O)(=O)C.C1C=C[NH+]=CC=1.Br[Br-]Br.[BH4-].[Na+]>C1COCC1>[Cl:9][C:7]1[S:6][C:5]2[S:10](=[O:11])(=[O:12])[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH2:2][CH:1]([OH:3])[C:4]=2[CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 4311764Sodium borohydrideHCID 19434004HCID 19434004, compound

Product 1

HCID 19434001HCID 19434001, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
3 °C

Procedure

The product from Step B (4.20 g, 12.14 mmol) was dissolved in THF (40 mL) containing 30% HBr in acetic acid (0.1 equiv, 0.25 mL) and cooled to 3° C. A solution of pyridinium bromide perbromide (4.32 g, 13.52 mmol) in THF (20 mL) was added and the reaction mixture allowed to warm to room temperature. The THF was evaporated and the residue dissolved in ethanol (40 mL); this solution was cooled (3° C.), sodium borohydride (pellets, 3.25 g, 86.03 mmol) added and the reaction mixture stirred at 5° C. for 1 hr followed by heating at reflux temperature for 1 hr. The reaction mixture was evaporated to a residue which was suspended in water and the pH of this suspension was adjusted to 7 with saturated aqueous ammonium chloride. This mixture was extracted with ethyl acetate (3×50 mL) and the combined extracts were dried (MgSO4). The products from two such reactions were purified by column chromatography (silica gel, 1:1 ethyl acetate/hexane) to give the desired product (3.6 g), mp 127°-132° C.; this material was used in the next reaction.

Workup

  1. temperatureto warm to room temperature
  2. customThe THF was evaporated
  3. dissolutionthe residue dissolved in ethanol (40 mL)
  4. additionadded
  5. temperatureby heating
  6. temperatureat reflux temperature for 1 hr
  7. customThe reaction mixture was evaporated to a residue which
  8. extractionThis mixture was extracted with ethyl acetate (3×50 mL)
  9. dry with materialthe combined extracts were dried (MgSO4)
  10. customThe products from two such reactions were purified by column chromatography (silica gel, 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0f7f972a75714b93849af90b6be8d8ea
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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