HCID 22347462, compound → HCID 66935050, compound

HRID 554759Notes

Reaction equation

HRID 554759 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-1d4c02e6be484db0a7dec5dd88d0ebab
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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