HCID 22347462, compound → HCID 66935050, compound

HRID 1892813Notes

Reaction equation

HRID 1892813 reaction equation
[NH2:1][S:2]([C:5]1[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:7]([NH:18]C(OCC2C=CC=CC=2)=O)[CH:6]=1)(=[O:4])=[O:3]>O1CCCC1.[C].[Pd]>[NH2:18][C:7]1[CH:6]=[C:5]([S:2]([NH2:1])(=[O:3])=[O:4])[CH:17]=[CH:16][C:8]=1[C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10]

Participants

4

Reactant 1

HCID 22347462HCID 22347462, compound

Product 1

HCID 66935050HCID 66935050, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 4-aminosulfonyl-2-(benzyloxycarbonyl)aminobenzoate (5.0 g) in tetrahydrofuran solution (50 ml), 5% palladium carbon (500 mg) was added and the mixture was stirred under hydrogen atmosphere at room temperature for 1 hour. The insoluble compound was filtered out, and the filtrate was concentrated. The residue was diluted with ethyl acetate, then the insoluble compound was again filtered out. The filtrate was concentrated, and the residue was recrystallized from ethyl acetate/hexane to obtain the title compound (2.9 g).

Workup

  1. filtrationThe insoluble compound was filtered out
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was diluted with ethyl acetate
  4. filtrationthe insoluble compound was again filtered out
  5. concentrationThe filtrate was concentrated
  6. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-eb15c2983abf479193320c2a19b16057
Source dataset
uspto-grants-2013_08
Patent number
US08507714B2

Reaction notes

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