(S)-3-(2-Benzyloxy-4-nitro-benzenesulfonylamino)-succinamic acid tert-butyl ester → (S)-3-(4-Amino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester

HRID 1814345Notes

Reaction equation

HRID 1814345 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][C@H:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:15])=[O:14])[C:9]([NH2:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Ni]>[C:1]([O:5][C:6](=[O:33])[CH2:7][C@H:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:14])=[O:15])[C:9]([NH2:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69692796(S)-3-(2-Benzyloxy-4-nitro-benzenesulfonylamino)-succinamic acid tert-butyl ester

Product 1

HCID 69692844(S)-3-(4-Amino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-3-(2-benzyloxy-4-nitro-benzenesulfonylamino)-succinamic acid tert-butyl ester (1.30 g, 2.70 mmol) in THF (75 mL) was shaken with Raney Nickel (0.50 g) under H2 (33 psi) for 18 h using a Parr apparatus. The reaction mixture was filtered through celite and concentrated. (S)-3-(4-Amino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester was obtained (1.20 g, 98%) as an off white solid. MS (APCI) m/z 448.1 (M−1).

Workup

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

Sources & evidence

ORD record
ord-59d89215924c42a897c45113040e0afb
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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