Hydrochloric Acid → HCID 22457591, compound

HRID 2184790Notes

Reaction equation

HRID 2184790 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:18]=[CH:17][CH:16]=[CH:15][CH2:14][N:13]2[C:19]([OH:21])=[O:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].Cl>O.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:18]=[CH:17][C:16]([C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])=[CH:15][CH2:14][N:13]2[C:19]([OH:21])=[O:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 22457584HCID 22457584, compound

Product 1

HCID 22457591HCID 22457591, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The 1-[(4-methoxyphenyl)sulfonyl]-diazepine-2-carboxylic acid (0.570 g, 1.33 mmol) is dissolved in water (5 mL) and p-dioxane (10 mL). Triethyl amine (0.74 mL, 5.32 mmol) and benzyl chloroformate (0.228 mL, 1.59 mmol) are next added. The reaction mixture is stirred overnight at room temperature, and then the solution is acidified with 1N HCl to pH˜1 and 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 70% (95% water, 5% acetonitrile, 0.1% formic acid) and 30% (80% acetonitrile, 20% water) as the eluent.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic extracts are dried (Na2SO4)
  3. concentrationconcentrated down to an oil
  4. customThe oil is purified by HPLC with a reverse phase column

Sources & evidence

ORD record
ord-1beba14f3b644f588cd5f159e1c9226d
Source dataset
uspto-grants-2002_06
Patent number
US06399598B1

Reaction notes

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