Citric Acid → HCID 86672794, compound

HRID 1755093Notes

Reaction equation

HRID 1755093 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20]([NH2:26])([C:23](=[O:25])[NH2:24])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:27](Cl)(Cl)=[S:28].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH2:19][C:20]2([NH:26][C:27](=[S:28])[NH:24][C:23]2=[O:25])[CH2:21][CH2:22]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 10040ThiophosgeneHCID 81531DiisopropylethylamineHCID 10562199tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylate

Product 1

HCID 86672794HCID 86672794, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Diisopropylethylamine (1.67 ml, 9.84 mmol) was added to a solution of 4-amino-4-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 4.1 mmol) in THF (10 ml) at 0° C., and thiophosgene (0.376 ml, 4.9 mmol) was further added dropwise slowly. The reaction solution was warmed to room temperature and stirred overnight. A 10% aqueous citric acid solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layers were combined and dried over magnesium sulfate, and the solvent was then distilled off. The residue was purified by silica gel column chromatography to give 4-oxo-2-thioxo-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (944 mg, 81%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent was then distilled off
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-23ced1aad15b4387a8ce8e0038ef116a
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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