Stannous chloride dihydrate → Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(4-chloro-2-aminobenzyl)amino]propionate

HRID 1264593Notes

Reaction equation

HRID 1264593 reaction equation
[OH:1][CH2:2][CH:3]([N:8]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[N+:17]([O-])=O)[C:4]([O:6][CH3:7])=[O:5].O.O.Cl[Sn]Cl>CO>[OH:1][CH2:2][CH:3]([N:8]([S:20]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)(=[O:22])=[O:21])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[NH2:17])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrate2×HCID 18612795Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(4-chloro-2-nitrobenzyl)amino]propionate

Product 1

HCID 18612723Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(4-chloro-2-aminobenzyl)amino]propionateYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.454 g (1 mmol) of methyl 3-hydroxy-2-[(4-methoxy-benzenesulfonyl)-(4-chloro-2-nitrobenzyl)amino]propionate and 0.451 g (2 mmol) of SnCl2.2H2O in 12 ml of methanol was refluxed for 2 hours. An additional 0.451 g (2 mmol) of SnCl2.2H2O was added and the mixture refluxed for 2 hours. The solvent was removed and ethyl acetate added. The mixture was neutralized with 1 N NaHCO3 and then stirred for 1 hour and filtered. The ethyl acetate layer was separated and washed with H2O, brine and dried with Na2SO4. The solvent was removed to give 0.42 g of solid which was chromatographed on thick layer silica gel plates with hexane-ethyl acetate (45:55) as solvent to give 60 mg of product (RF0.66) as a glass, m.p. 99°-112° C. Anal. for C18H21ClN2O6S: Calc'd: C, 50.4; H, 4.9; N, 6.5; Found: C, 49.7; H, 4.9; N, 6.4.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturethe mixture refluxed for 2 hours
  3. customThe solvent was removed
  4. additionethyl acetate added
  5. filtrationfiltered
  6. customThe ethyl acetate layer was separated
  7. washwashed with H2O, brine
  8. dry with materialdried with Na2SO4
  9. customThe solvent was removed

Sources & evidence

ORD record
ord-a0c6a9f4af3d4000970877cdefa4d3ac
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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