Triethylamine → N-(4-nitrobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamide

HRID 1356428

Reaction equation

HRID 1356428 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][CH:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[N+:28]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1)([O-:30])=[O:29].C(N(CC)CC)C>C1COCC1.CN(C=O)C>[N+:28]([C:31]1[CH:32]=[CH:33][C:34]([CH2:35][NH:36][C:13]([CH:9]2[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:12][CH2:11][S:10]2)=[O:15])=[CH:37][CH:38]=1)([O-:30])=[O:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 291474-NitrobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 46440943-(tert-Butoxycarbonyl)-1,3-thiazolidine-2-carboxylic acid

Product 1

HCID 21918695N-(4-nitrobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamideYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-(t-butoxycarbonyl)thiazolidine-2-carboxylic acid (1 g, 4.3 mmol) and carbonyldiimidazole (0.7 g, 4.3 mmol) are dissolved in THF (10 ml). The mixture is agitated for 1 hour at ambient temperature. 4-nitrobenzylamine (0.81 g, 4.3 mmoles) and triethylamine (0.6 ml. 0.43 g, 4.3 mmoles) in suspension in 10 ml of a THF and DMF mixture (1/1) are added to the preceding solution and the whole is heated under reflux for 5 hours. The solvents are then evaporated off under reduced pressure. The residue is taken up in 25 ml of ethyl acetate and washed 3 times with 15 ml of water. The organic phase is dried and the solvent is evaporated off under reduced pressure. The product obtained is purified on silica gel in a dichloromethane/methanol mixture (95/5). N-(4-nitrobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamide is obtained in the form of a pale yellow oil with a yield of 80% (1.25 g).

Workup

  1. temperaturethe whole is heated
  2. temperatureunder reflux for 5 hours
  3. customThe solvents are then evaporated off under reduced pressure
  4. washwashed 3 times with 15 ml of water
  5. customThe organic phase is dried
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe product obtained
  8. customis purified on silica gel in a dichloromethane/methanol mixture (95/5)

Sources & evidence

ORD record
ord-ecadd33468574b3daf5ff3f523e3314c
Source dataset
uspto-grants-2003_07
Patent number
US06586454B2

Linked notes

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