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

HRID 1180555Notes

Reaction equation

HRID 1180555 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 methyl 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-nitrobenzyl)amino]propionate (1.5 g, 3.53 mmol) in dry ethanol (5 ml) was added ammonium formate (1.12 g , 17.69 mmol) followed by the addition of 10% palladium on carbon (0.50 g). The mixture was stirred overnight at room temperature and then heated at 80° C. for 2 hours. The mixture was filtered through diatomaceous earth and the filtrate concentrated to dryness in vacuo to give a semisolid. Trituration with ethyl acetate gave 0.65 g (47%) of white crystals, m.p. 138-140° C.

Workup

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

Sources & evidence

ORD record
ord-79a10294135d4890b9d73c32de390444
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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