Hydroxylamine → HCID 178490317, compound

HRID 1634710Notes

Reaction equation

HRID 1634710 reaction equation
[NH2:1][OH:2].[CH3:3][O:4][C:5]1[CH:33]=[CH:32][C:8]([CH2:9][CH2:10][N:11]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:12][CH2:13][C:14]([O:16]C)=O)=[CH:7][CH:6]=1>>[OH:2][NH:1][C:14](=[O:16])[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:33][CH:32]=1)[S:18]([C:21]1[CH:22]=[CH:23][C:24]([C:27]2[NH:31][N:30]=[N:29][N:28]=2)=[CH:25][CH:26]=1)(=[O:20])=[O:19]

Participants

3

Reactant 2

HCID 787HydroxylamineHCID 178500791HCID 178500791, compound

Product 1

HCID 178490317HCID 178490317, compound

Procedure

Freshly prepared NH2OH solution (1 M in MeOH) (1.5 mL) was added to methyl 3-[(4-methoxyphenethyl)-(4-(tetrazol-5yl)-benzenesulfonyl)-amino]-propionate (112 mg, 0.25 mmol). After stirring at room temperature for 18 h, the reaction mixture was partitioned between 1 N HCl solution (20 mL) and ethyl acetate (30 mL). Two phases were separated and the aqueous layer was extracted with another 30 mL of ethyl acetate. Combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give N-hydroxy-3-[(4-methoxyphenethyl)-(4-(tetrazol-5yl)benzene-sulfonyl)amino]-propionamide (52 mg, 0.12 mmol). NMR (360 MHz, DMSO-d6) δ 10.46 (s, 1H), 8.74 (br s, 1H), 8.22 (d, J=8.4 Hz, 2H), 7.99 (d, J=8.7 Hz, 2H), 7.10 (d, J=8.2 Hz, 2H), 6.81 (d, J=8.2 Hz, 2H), 3.69 (s, 3H), 3.42 (t, J=7.5 Hz, 2H), 3.31 (t, J=7.9 Hz, 2H), 2.70 (t, J=7.6 Hz, 2H), 2.25 (t, J=7.5 Hz, 2H).

Workup

  1. customthe reaction mixture was partitioned between 1 N HCl solution (20 mL) and ethyl acetate (30 mL)
  2. customTwo phases were separated
  3. extractionthe aqueous layer was extracted with another 30 mL of ethyl acetate
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-877046e7537f4af39f010ef98c05572e
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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