Citric Acid → HCID 49849089, compound

HRID 1966100Notes

Reaction equation

HRID 1966100 reaction equation
[OH:1][N:2]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:23]([O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:37][CH2:38][C@H:39]([N:43]2[CH2:48][CH2:47][N:46]([S:49]([CH3:52])(=[O:51])=[O:50])[CH2:45][CH2:44]2)[C:40]([OH:42])=O)(=[O:36])=[O:35])=[CH:30][CH:29]=1)[C:24]#[C:25][CH3:26].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[CH2:23]([O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:37][CH2:38][C@H:39]([N:43]2[CH2:48][CH2:47][N:46]([S:49]([CH3:52])(=[O:51])=[O:50])[CH2:45][CH2:44]2)[C:40]([NH:2][OH:1])=[O:42])(=[O:35])=[O:36])=[CH:30][CH:29]=1)[C:24]#[C:25][CH3:26]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66870897HCID 66870897, compound

Product 1

HCID 49849089HCID 49849089, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

120 mg (0.9 mmol) of 1-hydroxybenzotriazole and 170 mg (0.9 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride are added to a solution of 340 mg (0.7 mmol) of (S)-3-(4-but-2-ynyloxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoic acid in 8 ml of dimethylformamide. The reaction medium is stirred for 30 min, and then 120 mg (0.8 mmol) of O-tert-butyldimethysilylhydroxylamine in 3 ml of dimethylformamide are added. The reaction medium is then stirred at ambient temperature for 20 h, and then hydrolyzed with 2 ml of water and 2 ml of a 5% aqueous solution of citric acid. After stirring for 30 min, a saturated aqueous solution of sodium hydrogen carbonate is added to pH=8, and then the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and concentrated. The residue is taken up in dichloromethane, filtered, and then dried under vacuum. 80 mg (23%) of (S)-3-(4-but-2-ynyloxybenzenesulfonylamino)-N-hydroxy-2-(4-methanesulfonylpiperazin-1-yl)propionamide are obtained in the form of a white solid with a melting point of 150° C.

Workup

  1. stirringThe reaction medium is then stirred at ambient temperature for 20 h
  2. stirringAfter stirring for 30 min
  3. extractionthe reaction medium is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationfiltered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-f2e385dda7ab46e8ad1099339ec4fceb
Source dataset
uspto-grants-2013_04
Patent number
US08420632B2

Reaction notes

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