Hydrochloric Acid → HCID 86755842, compound

HRID 1954058Notes

Reaction equation

HRID 1954058 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:18]=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[CH:15][CH2:14][N:13]2[C:30](O)=[O:31])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.Cl.[NH2:45][OH:46].C(N(CC)CC)C.NO.Cl>C(Cl)Cl.O.C1COCC1>[OH:46][NH:45][C:30]([N:13]1[CH2:14][CH:15]=[C:16]([S:19]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)(=[O:21])=[O:20])[CH:17]=[CH:18][N:12]1[S:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)(=[O:10])=[O:11])=[O:31]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 701037231,5-Di-[(4methoxyphenyl)sulfonyl]-diazepine-2-carboxylic acid

Product 1

HCID 86755842HCID 86755842, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 1,5-di-[(4-methoxyphenyl)sulfonyl]-diazepine-2-carboxylic acid (0.60 g, 1.24 mmol) is dissolved in methylene chloride (15 mL) at room temperature followed the addition of oxalyl chloride (0.32 mL, 2.54 mmol) and slow addition of DMF (0.09 g, 1.24 mmol). This solution is stirred for 30 minutes at room temperature. In a separate flask, hydroxylamine hydrochloride (0.34 g, 5.0 mmol) in water (5 mL) and THF (7 mL) is stirred at 0° C., and then triethylamine (1.0 mL, 6 equiv) is added. This solution is stirred for 15 minutes. The acid chloride solution is added to the hydroxylamine solution at 0° C. and then warmed up to room temperature and stirred for 3 hours. The solution is acidified to pH-1 with 1N HCl, poured into water and extracted with methylene chloride. The organic extracts are dried (Na2SO4) and concentrated down to an oil. The oil is purified by HPLC with a reverse phase column using 65% (95% water, 5% acetonitrile, 0.1 % formic acid) and 35% (80% acetonitrile, 20% water) as the eluent. MS (ESI): 500 (M+H+), 517 (M+NH4+).

Workup

  1. stirringThis solution is stirred for 15 minutes
  2. temperaturewarmed up to room temperature
  3. stirringstirred for 3 hours
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic extracts are dried (Na2SO4)
  6. concentrationconcentrated down to an oil
  7. customThe oil is purified by HPLC with a reverse phase column

Sources & evidence

ORD record
ord-445153028b97476894435b86647479fa
Source dataset
uspto-grants-2000_09
Patent number
US06121258

Reaction notes

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