Ethyl Acetate → Methyl [(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate

HRID 1264583Notes

Reaction equation

HRID 1264583 reaction equation
[OH:1][CH2:2][CH:3]([N:8]([S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O)[C:4]([O:6][CH3:7])=[O:5].C([O-])=O.[NH4+].C(OCC)(=O)C>C(O)C.[Pd]>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][N:8]([S:19]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)(=[O:21])=[O:20])[CH:3]([CH2:2][OH:1])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 18612897Methyl 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-nitrobenzyl)amino]propionate

Product 1

HCID 18612758Methyl [(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionateYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture under nitrogen of 1.5 g (3.53 mmol) of methyl 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-nitrobenzyl)amino]propionate in 5 ml of dry ethanol was added 1.12 g (17.69 mmol) of ammonium formate followed by the addition of 0.50 g of 10% palladium on carbon. The mixture was stirred overnight at room temperature and heated at 80° C. for 2 hours. The mixture was filtered through diatomaceous earth and the filtrate concentrated to dryness under vacuum to give a semisolid. Trituration with ethyl acetate gave 0.65 g (47%) of white crystals, m.p. 138-140° C.; Anal. for C18H22N2O6S: Calc'd: C, 54.8; H, 5.6; N, 7.1; Found: C, 53.0; H, 5.6; N, 6.8.

Workup

  1. temperatureheated at 80° C. for 2 hours
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. concentrationthe filtrate concentrated to dryness under vacuum
  4. customto give a semisolid

Sources & evidence

ORD record
ord-49de9fc019c14c5bb0f9a65ce205c1ab
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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