Propionic Acid → HCID 10617057, compound

HRID 1463262Notes

Reaction equation

HRID 1463262 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[S:12][CH:11]=[C:10]([S:13]([NH2:16])(=[O:15])=[O:14])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25](O)(=[O:28])[CH2:26][CH3:27].CCN=C=NCCCN(C)C>C(OCC)(=O)C.C1COCC1>[C:25]([O:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[S:12][CH:11]=[C:10]([S:13]([NH2:16])(=[O:15])=[O:14])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1)(=[O:28])[CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 1032Propionic AcidHCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10612967HCID 10612967, compound

Product 1

HCID 10617057HCID 10617057, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.10 g (0.35 mmol) of 5-(4-hydroxybenzoyl)-3-thiophene sulfonamide, 85 mL (1.05 mmol) of pyridine, 26 mL (0.35 mmol) of propionic acid and 70 mg (0.37 mmol) of EDCI were added to 3.5 mL of THF. The reaction was stirred at rt for 46 h. The solution was diluted with ethyl acetate and washed with water (3×) followed with brine. The solution was dried over MgSO4 and the solvent removed under vacuum. Flash chromatography utilizing 1:1 ethyl acetate/hexane recovered 77 mg of 5-(4-propionoxybenzoyl)-3-thiophene sulfonamide as a clear colorless oil.

Workup

  1. washwashed with water (3×)
  2. dry with materialThe solution was dried over MgSO4
  3. customthe solvent removed under vacuum
  4. customrecovered 77 mg of 5-(4-propionoxybenzoyl)-3-thiophene sulfonamide as a clear colorless oil

Sources & evidence

ORD record
ord-b31569de7a274dac80840c3e8bf8252e
Source dataset
uspto-grants-1994_04
Patent number
US05300499

Reaction notes

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