Ammonia → Benzyl 4-[(3-amino-3-oxopropyl)(tert-butoxycarbonyl)amino]piperidin-1-carboxylate

HRID 2366554노트

반응식

HRID 2366554 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][CH2:19][C:20]([OH:22])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:32]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.N>CN(C=O)C>[NH2:32][C:20](=[O:22])[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH:14]1[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:16][CH2:15]1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68418183HCID 68418183, 화합물

생성물 1

HCID 68425948Benzyl 4-[(3-amino-3-oxopropyl)(tert-butoxycarbonyl)amino]piperidin-1-carboxylate수율 83.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of N-{1-[(benzyloxy)carbonyl]piperidin-4-yl}-N-(tert-butoxycarbonyl) -β-alanine (4.06 g) obtained in Example 45b), WSC (1.92 g) and HOBt.NH3 (1.52 g) in DMF (40 mL) was stirred overnight at room temperature, and DMF was distilled off under reduced pressure. The residue was diluted with dichloromethane, washed with an aqueous saturated sodium bicarbonate solution and saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (from ethyl acetate/hexane=1/1 to ethyl acetate) to obtain the title compound (3.38 g, 83%) as a white amorphous powder.

후처리

  1. distillationDMF was distilled off under reduced pressure
  2. additionThe residue was diluted with dichloromethane
  3. washwashed with an aqueous saturated sodium bicarbonate solution and saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (from ethyl acetate/hexane=1/1 to ethyl acetate)

출처 및 근거

ORD 기록
ord-464ff1a859504909b9f46953ad6d9deb
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697865B2

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