Hydroxylamine → Acetic acid 2-hydroxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-azepan-3-ylmethyl ester

HRID 1872233Notes

Reaction equation

HRID 1872233 reaction equation
[C:1]([O:4][CH2:5][CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:7]1[C:24]([OH:26])=O)(=[O:3])[CH3:2].C(N(CC)C(C)C)(C)C.[OH:36][NH2:37].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.C(OCC)(=O)C>[OH:36][NH:37][C:24]([CH:7]1[CH:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])=[O:26]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 186896413-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid

Product 1

HCID 53777204Acetic acid 2-hydroxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-azepan-3-ylmethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid (107 mg, 0.28 mmoL) in 5.6 mL dichloromethane was added N,N-Diisopropyl ethyamine (0.195 mL, 1.12 mmoL). This solution was cooled to 0° C. and Hydroxyl amine (58.4 mg, 0.84 mmoL) was added followed by PyBroP (155 mg, 0333 mmoL). The reaction was warmed to ambient temperature after 15 minutes and was stopped after 5.5 hours. The residue was diluted with ethyl acetate and washed sequentially with 0.5N HCl, and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (silica: 0.5% to 1.5% methanol in dichloromethane) to yield Acetic acid 2-hydroxycarbamoyl-1-(4-methoxy-benzene sulfonyl)-azepan-3-ylmethyl ester; MS: (M-H)- =399.

Workup

  1. temperatureThe reaction was warmed to ambient temperature after 15 minutes
  2. washwashed sequentially with 0.5N HCl, and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography (silica: 0.5% to 1.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-40688845014a4b52a0b57c794c78355a
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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