Ethanol → N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide

HRID 2209708Notes

Reaction equation

HRID 2209708 reaction equation
C([O:5][NH:6][C:7](=[O:35])[CH:8]([N:16]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]1[N:11]=[N:12][N:13]([CH3:15])[N:14]=1)(C)(C)C.C(O)C>C(Cl)Cl>[OH:5][NH:6][C:7](=[O:35])[CH:8]([N:16]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:9][C:10]1[N:11]=[N:12][N:13]([CH3:15])[N:14]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 22907048N-(t-butyloxy)-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide

Product 1

HCID 22907172N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-(t-butyloxy)-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide (0.77 g, 1.55 mmol) is dissolved in methylene chloride (2.0 mL) and ethanol (0.1 mL) in a glass sealed tube, and the reaction is cooled to 0° C. Hydrochloric acid gas (from a lecture bottle) is bubbled through the solution for 20 minutes, and then the tube is sealed at room temperature for 3 days. After that time, the solvent is removed, and the reaction is partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase is dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (2% methanol/methylene chloride) to give N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide, m.p. 72°-75° C.

Workup

  1. customHydrochloric acid gas (from a lecture bottle) is bubbled through the solution for 20 minutes
  2. customthe tube is sealed at room temperature for 3 days
  3. customAfter that time, the solvent is removed
  4. customthe reaction is partitioned between ethyl acetate and saturated sodium bicarbonate
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (2% methanol/methylene chloride)

Sources & evidence

ORD record
ord-9ddfede04a884313800b0101da86db49
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

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