Tetrahydrofuran → 3-(4-amino-2-hydroxy-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester

HRID 1814313Notes

Reaction equation

HRID 1814313 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:18]=1[O:26]CC1C=CC=CC=1)(=[O:16])=[O:15])[C:9]([NH:11][CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].C1COCC1>[Pd].CO>[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[OH:26])(=[O:15])=[O:16])[C:9]([NH:11][CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 696920283-(2-benzyloxy-4-nitro-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 696924193-(4-amino-2-hydroxy-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl esterYield 109.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.0 g (1.91 mmol) 3-(2-benzyloxy-4-nitro-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester from Route D, 0.2 g 20% Pd/C, and 75 mL of a 1:1 mixture of THF:MeOH was shaken under 50 psi H2 gas for 4.5 h. TLC analysis showed reaction complete. The reaction was filtered to remove catalyst and the solvent evaporated under reduced pressure to give 3-(4-amino-2-hydroxy-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester 0.78 g (100%) as a light yellow foam. MS (APCI) m/z 402 (M−1).

Workup

  1. customreaction complete
  2. filtrationThe reaction was filtered
  3. customto remove catalyst
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-2cdee91d461f4ab8a0507b1cf09ce14a
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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