Ethanol → HCID 22324080, compound

HRID 1767672Notes

Reaction equation

HRID 1767672 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)(=[O:11])=[O:10])[C:5](O)=[O:6].CCO.ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1.[Pd]>[CH2:3]([CH:4]1[C:5](=[O:6])[NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:9](=[O:11])(=[O:10])[NH:8]1)[CH:2]([CH3:21])[CH3:1]

Participants

7

Reactant 4

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 3140382HCID 3140382, compound

Product 1

HCID 22324080HCID 22324080, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of N-(3′-methyl-1′-carboxybutyl)-2-nitrobenzenesulfonamide (6.7 g; 21.2 mmol) and 10% Pd/C (200 mg) in abs. EtOH was hydrogenated at 1 bar. The reaction mixture was filtered through celite and evaporated to dryness. A solution of the crude product in dry THF (50 ml) at 0° C. was added N-hydroxysuccinimide (2.53 g; 22 mmol) and DCC (4.54 g; 22 mmol). The reaction mixture was slowly warmed to rt. and left with stirring over night. The reaction mixture was filtered and the solid material was washed with THF. The combined organic fractions were evaporated to dryness and the remanense added H2O and extracted with EtOAc. The combined organic fractions were dried (Na2SO4) and evaporated to dryness to give 3 g (53%) product.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated to dryness
  3. waitand left
  4. filtrationThe reaction mixture was filtered
  5. washthe solid material was washed with THF
  6. customThe combined organic fractions were evaporated to dryness
  7. additionthe remanense added H2O
  8. extractionextracted with EtOAc
  9. dry with materialThe combined organic fractions were dried (Na2SO4)
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-b0c8ae02f21146ba809e2e07a55a405f
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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