3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic tert-butyl ester → 3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

HRID 1814296Notes

Reaction equation

HRID 1814296 reaction equation
[C:1]([O:5][C:6](=[O:37])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][C:20]=1[O:29]CC1C=CC=CC=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:37])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][C:20]=1[OH:29])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 225040833-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 865882053-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl esterYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(4-Acetylamino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (0.99 g, 1.8 mmol) was dissolved in 50 mL methanol and 20% Pd/C (0.09 g) is added. The reaction was placed under 50 psi of hydrogen for approximately 1 hour. The reaction was filtered and concentrated in vacuo. The crude product was chromatographed with 2:1 ethyl acetate/hexane to yield 3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester 0.7 g (85%) of an brown solid. MS (APCI) m/z 444.2 (M−1).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude product was chromatographed with 2:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-d372cf0802794e9faddf5b2efb2cc893
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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