1,1'-Carbonyldiimidazole → tert-Butyl 4-carbamoyl-1,1-dioxo-1,3-thiazolidine-3-carboxylate

HRID 624985Notes

Reaction equation

HRID 624985 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[C:13]([O:17][C:18]([N:20]1[CH:24]([C:25](O)=[O:26])[CH2:23][S:22](=[O:29])(=[O:28])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[C:25]([CH:24]1[CH2:23][S:22](=[O:29])(=[O:28])[CH2:21][N:20]1[C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])(=[O:26])[NH2:3]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 235209253-tert-Butoxycarbonyl-1,1-dioxo-1,3-thiazolidine-4-carboxylic acid

Product 1

HCID 90204869tert-Butyl 4-carbamoyl-1,1-dioxo-1,3-thiazolidine-3-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Carbonyldiimidazole (520 mg, 3.21 mmol) was added to an ice cold solution of 3-tert-butoxycarbonyl-1,1-dioxo-1,3-thiazolidine-4-carboxylic acid (Example 127 b, 304 mg, 1.15 mmol) in DMF (1 mL). After 5 min. the mixture was warmed to ambient temperature and stirred for 2 h. Gaseous NH3 was bubbled for 10 min through the solution while the temperature was kept below 20° C. Stirring was continued for 12 h at ambient temperature. The reaction mixture was poured into 30 mL ice/water/1N HCl and extracted with EtOAc (2×30 mL). The combined extracts were washed with ice/brine (20 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (197 mg, 65%) as white solid, MS (ESI) m/e=263.1 [M−H−].

Workup

  1. customGaseous NH3 was bubbled for 10 min through the solution while the temperature
  2. customwas kept below 20° C
  3. stirringStirring
  4. waitwas continued for 12 h at ambient temperature
  5. additionThe reaction mixture was poured into 30 mL ice/water/1N HCl
  6. extractionextracted with EtOAc (2×30 mL)
  7. washThe combined extracts were washed with ice/brine (20 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb000d5e99724e4aaa0f74ca6ae8900b
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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