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4-Methylmorpholine → HCID 131717889, compound

HRID 324160
Notes
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Reaction equation

HRID 324160 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 13670087N-(1,2,2,2-Tetrachloroethoxycarbonyloxy)succinimideHCID 88219684HCID 88219684, compound

Product 1

HCID 131717889HCID 131717889, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 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-ddcfbea3febe461cb1a2ef3be433772d
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06217845B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes