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

HRID 1814344Notes

Reaction equation

HRID 1814344 reaction equation
C(Cl)Cl.[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[S:21](Cl)(=[O:23])=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:25]([O:29][C:30](=[O:37])[CH2:31][C@H:32]([NH2:36])[C:33]([NH2:35])=[O:34])([CH3:28])([CH3:27])[CH3:26].N1C=CC=CC=1>C(OCC)(=O)C>[C:25]([O:29][C:30](=[O:37])[CH2:31][C@H:32]([NH:36][S:21]([C:13]1[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=1[O:11][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:23])=[O:22])[C:33]([NH2:35])=[O:34])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7019655L-Aspartic alpha-amide beta-t-butyl esterHCID 225039842-Benzyloxy-4-nitro-benzenesulfonyl chloride

Product 1

HCID 69692796(S)-3-(2-Benzyloxy-4-nitro-benzenesulfonylamino)-succinamic acid tert-butyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature CH2Cl2 solution (50 mL) of 2-benzyloxy-4-nitro-benzenesulfonyl chloride from Route J (2.62 g, 8.0 mmol) was added (S)-3-amino-succinamic acid tert-butyl ester (1.50 g, 8.0 mmol) and pyridine (2.60 mL). The reaction mixture was allowed to stir for 12 h at room temperature. The reaction was then diluted with ethyl acetate (200 mL) and washed with 5% citric acid and then saturated NaHCO3. The organic phase was dried (MgSO4), and then the solvent was removed under vacuum. The resulting crude product was purified using silica gel flash chromatography (40% hexanes in EtOAc). (S)-3-(2-Benzyloxy-4-nitro-benzenesulfonylamino)-succinamic acid tert-butyl ester was obtained in 43% yield (1.66 g) as an off white foam. MS (APCI) m/z 478.3 (M−1).

Workup

  1. washwashed with 5% citric acid
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe solvent was removed under vacuum
  4. customThe resulting crude product was purified

Sources & evidence

ORD record
ord-cb860a1b13a44a35ad8528136398884d
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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