(S)-3-(4-Acetylamino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester → (S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-succinamic acid tert-butyl ester

HRID 1814347Notes

Reaction equation

HRID 1814347 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][C@H:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][C:17]=1[O:26]CC1C=CC=CC=1)(=[O:15])=[O:14])[C:9]([NH2:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:5][C:6](=[O:34])[CH2:7][C@H:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][C:17]=1[OH:26])(=[O:15])=[O:14])[C:9]([NH2:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69691767(S)-3-(4-Acetylamino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester

Product 1

HCID 69692146(S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-succinamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester (0.92 g, 2.0 mmol) in THF (50 mL) was shaken with 20% Pd/C (0.090 g) under H2 (50 psi) for 5 h using Parr apparatus. The reaction mixture was filtered through celite and concentrated. (S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-succinamic acid tert-butyl ester was obtained (0.85 g, 98%) as an off white solid. MS (APCI) m/z 400.1 (M−1).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0a514fada6a64dc888ea53ecd8c2b8bc
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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