Stannous chloride dihydrate → (4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochloride

HRID 2121171Notes

Reaction equation

HRID 2121171 reaction equation
O.O.[Sn](Cl)[Cl:4].[CH3:6][O:7][C:8](=[O:32])[C@H:9]([CH2:28][CH2:29][S:30][CH3:31])[NH:10][C:11](=[O:27])[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[ClH:4].[CH3:6][O:7][C:8](=[O:32])[C@H:9]([CH2:28][CH2:29][S:30][CH3:31])[NH:10][C:11](=[O:27])[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 18666764(4-Nitro-2-phenylbenzoyl)methionine methyl ester

Product 1

HCID 69612387(4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tin(II) dichloride dihydrate (157 g, 696 mmol) was added to a solution of (4-nitro-2-phenylbenzoyl)methionine methyl ester (67.9 g, 175 mmol) in 500 mL ethyl acetate and the reaction mixture was heated at reflux for 1 hour. The reaction mixture was cooled to ambient temperature and stirring was continuted for 18 hours. The reaction mixture was concentrated to 200 mL, and 500 mL H2O was added. Solid NaHCO3 was added to pH 8 before extracting with ethyl acetate. The ethyl acetate extract were washed with 5% NaHCO3 and brine, dried over Na2SO4, and concentrated. The residue was dissolved in ether with a minimum of ethyl acetate added to keep the material in solution and treated with anhydrous HCl. The solid was collected and washed with ether to provide (4-amino-2-phenylbenzoyl)methionine methyl ester hydrochloride in 83% yield. MS m/e 359 (M+H)+. 1H NMR (d6-DMSO, 300 MHz) δ 1.83 (m, 2H), 1.99 (s, 3H), 2.23 (m, 2H), 3.63 (s, 3H), 4.33 (m, 1H), 7.03 (m, 2H), 7.35 (m, 6H), 7.48 (d, J=8 Hz, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated to 200 mL, and 500 mL H2O
  4. additionwas added
  5. additionSolid NaHCO3 was added to pH 8
  6. extractionbefore extracting with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washwere washed with 5% NaHCO3 and brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. dissolutionThe residue was dissolved in ether with a minimum of ethyl acetate
  12. additionadded
  13. additiontreated with anhydrous HCl
  14. customThe solid was collected
  15. washwashed with ether

Sources & evidence

ORD record
ord-020dd1bf56bc4c2c96a2f999b49a3d19
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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