Hydrochloric Acid → HCID 9931836, compound

HRID 1872226Notes

Reaction equation

HRID 1872226 reaction equation
[CH2:1]([C@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C@H:9]1[C:26]([OH:28])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:36][OH:37].C(N(CC)CC)C.Cl>C(Cl)Cl.C(OCC)(=O)C.O.O1CCCC1.CN(C)C=O>[CH2:1]([C@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C@H:9]1[C:26]([NH:36][OH:37])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 70289689HCID 70289689, compound

Product 1

HCID 9931836HCID 9931836, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

cis-3-Benzyl-1-(4-methoxybenzenesulfonyl)-azepane-2-carboxylic acid (146 mg, 0.36 mmol) was dissolved in 4-mL of anhydrous methylene chloride. Dimethylformamide (10-μL) was added followed by oxalyl chloride (0.36-mL of a 2.0 M solution, 0.72 mmol). The reaction was allowed to stir at room temperature for 30 minutes. In a separate flask, 2.0-mL of tetrahydrofuran was used to suspend hydroxylamine hydrochloride (125 mg, 1.8 mmol). 0.2-mL of water was added to dissolve the mixture. The solution was cooled on ice then triethylamine (290 mg, 2.88 mmol) was added. This solution was stirred at 0° C. for 30 minutes. The acid chloride solution was then added and the reaction stirred at 0° C. for an additional 30 minutes. 20-mL of ethyl acetate was added followed by 20-mL of 0.25 M hydrochloric acid. The layers were separated and the aqueous phase was extracted with another 20-mL of ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated to leave a clear colorless oil which was chromatographed (silica gel, 0-1% methanol in methylene chloride) to afford the title compound ((M+H)+ 419.2, (M+NH4)+ 436.2).

Workup

  1. dissolutionto dissolve the mixture
  2. temperatureThe solution was cooled on ice
  3. stirringThis solution was stirred at 0° C. for 30 minutes
  4. stirringthe reaction stirred at 0° C. for an additional 30 minutes
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with another 20-mL of ethyl acetate
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto leave a clear colorless oil which
  12. customwas chromatographed (silica gel, 0-1% methanol in methylene chloride)

Sources & evidence

ORD record
ord-f9be0fb83eac4e17ad54ad7c456d2b7c
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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