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

HRID 1814280Notes

Reaction equation

HRID 1814280 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].[H][H]>[Pd]>[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

4

Reactant 2

HCID 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 104.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(S)-3-(2-Benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (3.54 g) in TBF(50 mL) was treated with 20% Pd/C (0.30 g) at 50 psi hydrogen until uptake was complete. The reaction was filtered and the filtrate was evaporated to give (S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester as a colorless oil (3.01 g, 100%). 1H NMR (CDCl3) 8.82(s,1H), 7.63(d,1H), 7.44(t,1H), 6.98(m,2H), 5.95(d,1H), 4.62(bs,1H), 3.62(s,3H), 3.03(s,3H), 2.65-2.40(AB quartet, 2H), 1.43(s,9H).

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a8d3216c5b844a7eaeaef2e1acc0bbac
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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