4-Methylmorpholine → HCID 131717889, compound

HRID 1591305Notes

Reaction equation

HRID 1591305 reaction equation
C([C:8]1[CH:23]=[C:22]([NH:24][NH:25][C:26]([NH2:28])=[S:27])[CH:21]=[CH:20][C:9]=1[C:10]([O:12][N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19])=[O:11])(OC(C)(C)C)=O.CN1CCOCC1.C(=O)(OC(Cl)C(Cl)(Cl)[Cl:48])ON1C(=O)CCC1=O.C(OCC)(=O)C>C(#N)C.CCOCC>[ClH:48].[NH:24]([C:22]1[CH:23]=[CH:8][C:9]([C:10]([O:12][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][C:14]2=[O:19])=[O:11])=[CH:20][CH:21]=1)[NH:25][C:26]([NH2:28])=[S:27].[C:14]1(=[O:19])[N:13]([O:12][C:10](=[O:11])[C:9]2[CH:20]=[CH:21][C:22]([NH:24][NH:25][C:26]([NH2:28])=[S:27])=[CH:23][CH:8]=2)[C:17](=[O:18])[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 136700871-{[(1,2,2,2-Tetrachloroethoxy)carbonyl]oxy}pyrrolidine-2,5-dioneHCID 88219684HCID 88219684, compound

Product 1

HCID 131717889HCID 131717889, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

Synthesis of Succinimidyl BOC-4-thiosemicarbazidobenzoate [Hydrazinecarboxylic acid, 2-[[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxyl]carbonyl]phenyl]amino]thioxomethyl]-1,1-dimethylethyl ester]--To a solution of acid (1 equivalent) and N-methylmorpholine (1.1 equivalents) in acetonitrile was added a solution of succinimidyl tetrachloroethyl carbonate (1 equivalent) in acetonitrile. The reaction mixture was stirred at room temperature for 16 hours. Ethyl acetate was added to the reaction mixture and the homogeneous solution was washed with cold 5% citric acid, cold water, cold aqueous saturated sodium bicarbonate solution, cold water and cold brine. The organic phase was dried (MgSO4), filtered and concentrated to give a pale yellow oil. The oil was flash chromatographed on silica gel using hexanes/ethyl acetate as eluant. The product was isolated as a yellow oil which solidified on the addition of ether. The solids were isolated by filtration to give the desired product; yield 25%; m.p. 161°-163°.

Workup

  1. washthe homogeneous solution was washed with cold 5% citric acid, cold water, cold aqueous saturated sodium bicarbonate solution, cold water and cold brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a pale yellow oil
  6. customchromatographed on silica gel
  7. customThe product was isolated as a yellow oil which
  8. customThe solids were isolated by filtration

Sources & evidence

ORD record
ord-3076a8c7eecc4b15a70d21bc65c605c7
Source dataset
uspto-grants-1993_04
Patent number
US05206370

Reaction notes

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