Ammonia → (2S)-N-(tert-Butyloxycarbonyl)piperidine-2-carboxamide

HRID 1927802노트

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HRID 1927802 반응식
[C:1]([O:5][C:6](N1CCCC[C@H]1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:17].O[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=N1.CCN=C=NCCCN(C)C.Cl.N>C(Cl)Cl.CN(C=O)C>[C:1]([O:5][C:6]([NH:19][C:23]([C@@H:24]1[CH2:25][CH2:26][CH2:27][CH2:22][NH:21]1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 51534906(2S)-N-(tert-Butyloxycarbonyl)piperidine-2-carboxamide수율 57%

시약·촉매·용매 1

HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

(2S)—N-(tert-Butyloxycarbonyl)pipecolinic acid (3.0 g, 13.0 mmol) was dissolved in CH2Cl2/DMF (9:1, 150 ml). To this solution at 0° C. was added 1-hydroxybenzotriazole hydrate (2.0 g, 14.8 mmol) and water soluble carbodiimide (2.74 g, 13.7 mmol). After 1 h at 0° C. ammonia (35%, 25 ml) was added. After 18 h at 0° C. to room temperature the solvent was removed in vacuo and the residue was taken up in ethyl acetate (500 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 4% methanol, 96% chloroform) to give a white solid identified as the title compound (1.7 g, 7.4 mmol, 57%).

후처리

  1. customAfter 18 h at 0° C. to room temperature the solvent was removed in vacuo
  2. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (eluant: 4% methanol, 96% chloroform)
  6. customto give a white solid

출처 및 근거

ORD 기록
ord-1697183e0e4d4b59ba5c7d412c9ba43b
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183280B2

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