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

HRID 1244495

반응식

HRID 1244495 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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 I 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-carboxarnide is obtained in the form of a pale yellow oil with a yield of 80% (1.25 g).

후처리

  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)

출처 및 근거

ORD 기록
ord-40095553f27c4e399f8b0d5c146dad8c
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122535B2

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