Hydroxylamine → HCID 12074758, compound

HRID 1370742Notes

Reaction equation

HRID 1370742 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][C:13]([NH:15][C@H:16]([C:34](OC)=[O:35])[CH2:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([S:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:38][OH:39]>O1CCCC1.CO>[C:1]1([CH2:7][O:8][C:9](=[O:10])[NH:11][CH2:12][C:13]([NH:15][CH:16]([CH2:17][S:18]([C:21]2[CH:22]=[CH:23][C:24]([S:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:25][CH:26]=2)(=[O:19])=[O:20])[C:34]([NH:38][OH:39])=[O:35])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 131723935HCID 131723935, compound

Product 1

HCID 12074758HCID 12074758, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound of Example 16b (440 mg, 0.81 mmol) in tetrahydrofuran (9 mL) and methanol (3 mL) was added NH2OH (50% aqueous solution, 0.74 mL, 12 mmol). After stirring for 20 hours at room temperature, the solution was concentrated. Purification by flash chromatography (5:95 MeOH/CHCl3) yielded the title compound as a white solid (80 mg, 18%): Anal. Calcd. for C25H25N3O7S2.0.25 H2O: C, 54.78; H, 4.69; N, 7.67; S, 11.70. Found: C, 54.78; H, 4.72; N, 7.46; S, 11.53.

Workup

  1. concentrationthe solution was concentrated
  2. customPurification by flash chromatography (5:95 MeOH/CHCl3)

Sources & evidence

ORD record
ord-81e8a1966e6a4bc5b7f257cf421567de
Source dataset
uspto-grants-2003_06
Patent number
US06583299B1

Reaction notes

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