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Triethylamine → 4-Hydroxy-piperidine-1-carboxylic Acid 5-(4-chloro-benzoylamino)-pyridin-2-yl Ester

HRID 1831316
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HRID 1831316 반응식
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.C(NC1C=CC([O:33][C:34]([N:36]2[CH2:41][CH2:40][CH:39]([O:42][Si](C(C)(C)C)(C)C)[CH2:38][CH2:37]2)=O)=NC=1)(=O)C1C=CC=CC=1.C(N(CC)CC)C.CCCCCCC>CN(C)C=O>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:34]([N:36]3[CH2:41][CH2:40][CH:39]([OH:42])[CH2:38][CH2:37]3)=[O:33])=[N:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8900HeptaneHCID 695176994-(tert-Butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl EsterHCID 178522254HCID 178522254, 화합물

생성물 1

HCID 695188084-Hydroxy-piperidine-1-carboxylic Acid 5-(4-chloro-benzoylamino)-pyridin-2-yl Ester수율 43%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-chloro-N-(6-hydroxy-pyridin-3-yl)-benzamide (0.50 g, 2.00 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic acid 5-benzoylamino-pyridin-2-yl ester (0.90 g, 2.00 mmol) and triethylamine (0.20 g, 2.00 mmol) in dimethylformamide (10 mL) was stirred overnight at room temperature. The solvent was evaporated in vacuo. The residue was dissolved in dichloromethane, filtered over a short pad of silicagel and washed with ethyl acetate:heptane 50:50. The solvent was evaporated in vacuo and the residue was redissolved in acetonitrile and hydrofluoric acid (min. 40% in water, 0.50 mL) was added. After stirring overnight at room temperature the solvent was evaporated in vacuo. Dichloromethane and triethylamine (1 mL) were added and the solution was extracted twice with water, dried over sodium sulphate, filtered and evaporated in vacuo. Crystallisation from ethyl acetate:heptane yielded the title compound (321 mg, 43% yield).

후처리

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. filtrationfiltered over a short pad of silicagel
  4. washwashed with ethyl acetate:heptane 50:50
  5. customThe solvent was evaporated in vacuo
  6. dissolutionthe residue was redissolved in acetonitrile
  7. additionhydrofluoric acid (min. 40% in water, 0.50 mL) was added
  8. customwas evaporated in vacuo
  9. additionDichloromethane and triethylamine (1 mL) were added
  10. extractionthe solution was extracted twice with water
  11. dry with materialdried over sodium sulphate
  12. filtrationfiltered
  13. customevaporated in vacuo
  14. customCrystallisation from ethyl acetate

출처 및 근거

ORD 기록
ord-374da5f7e4e84adc86f050b695b91ce7
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07067517B2

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