Hydrochloric Acid → HCID 22457588, compound

HRID 1954061Notes

Reaction equation

HRID 1954061 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[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=3)(=[O:21])=[O:20])=[CH:15][CH2:14][N:13]2[C:28](O)=[O:29])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.Cl.[NH2:43][OH:44].C(N(CC)CC)C.ON.Cl>C(Cl)Cl.O.C1COCC1>[OH:44][NH:43][C:28]([N:13]1[CH2:14][CH:15]=[C:16]([S:19]([C:22]2[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=2)(=[O:20])=[O:21])[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:11])=[O:10])=[O:29]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 70103910HCID 70103910, compound

Product 1

HCID 22457588HCID 22457588, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 1-[(4-methoxyphenyl)sulfonyl]-5-(1-methyl-1H-imidazole-4-sulfonyl)-diazepine-2-carboxylic acid (0.35 g, 0.76 mmol) is dissolved in methylene chloride (10 mL) at room temperature followed the addition of oxalyl chloride (0.14 mL, 1.56 mmol) and the slow addition of DMF (0.058 mL, 0.76 mmol). This mixture is stirred for 30 minutes at room temperature. In a separate flask, hydroxylamine hydrochloride (0.21 g, 1.56 mmol) in water (2 mL) and THF (5 mL) are stirred at 0° C., and then triethylamine (0.634 mL, 4.56 mmol) is added. This mixture is stirred for 15 minutes. The acid chloride solution is added to the hydroxyl amine solution at 0° C. and the resulting solution is warmed 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 80% (95% water, 5% acetonitrile, 0.1 % formic acid) and 20% (80% acetonitrile, 20% water) as the eluent.

Workup

  1. stirringThis mixture is stirred for 15 minutes
  2. temperaturethe resulting solution is warmed 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-09d78d6856f942c7af5fbab64db229b6
Source dataset
uspto-grants-2000_09
Patent number
US06121258

Reaction notes

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