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

HRID 1814351Notes

Reaction equation

HRID 1814351 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][C@H:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25]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].O1CCCC1.[H][H]>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:33])[CH2:7][C@H:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 86588197(S)-3-(2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86588199(S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl esterYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 22.52 g (47.05 mmol) (S)-3-(2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester, 1 g 20% Pd on charcoal, 250 mL tetrahydrofuran and 250 mL ethanol was shaken under a 50 psig. hydrogen atmosphere for 26 h. The mixture was filtered through a pad of celite and concentrated. The residue was passed through a 100 g plug of silica eluting with 6:4 ethyl acetate:hexanes to give 17.5 g (45.05 mmol, 95.7%) of (S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester as a thick colorless oil. MS (APCI) m/z 387.0 (M−1).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8074e95f2deb4324834acb0e4f8c2771
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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