Triethylamine → HCID 178472518, 화합물

HRID 2242259노트

반응식

HRID 2242259 반응식
Cl.[CH2:2]([O:4][C:5]([C@H:7]1[CH2:10][C@@H:9]([NH2:11])[CH2:8]1)=[O:6])[CH3:3].C(N(CC)CC)C.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][N:29]=[C:28]([C:31]3[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=3)[N:27]=2)=[CH:22][CH:21]=1.C([BH3-])#N.[Na+]>CC(O)=O.C1COCC1>[CH2:2]([O:4][C:5]([C@H:7]1[CH2:10][C@@H:9]([NH:11][CH2:35][C:34]2[CH:33]=[CH:32][C:31]([C:28]3[N:27]=[C:26]([C:23]4[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=4)[O:30][N:29]=3)=[CH:38][CH:37]=2)[CH2:8]1)=[O:6])[CH3:3]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 592042754-[5-(4-Methylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehydeHCID 178472514HCID 178472514, 화합물

생성물 1

HCID 178472518HCID 178472518, 화합물수율 39,495.398%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of cis-3-amino-cyclobutanecarboxylic acid ethyl ester hydrochloride (50.7 mg, 0.282 mmol), triethylamine (0.058 mL, 0.423 mmol) and THF (2.5 mL) was stirred at room temperature for 30 minutes. 4-[5-(4-Methylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (74.5 mg, 0.282 mmol) and AcOH (0.50 mL) were added to the reaction mixture and stirred for 30 minutes. Sodium cyanoborohydride (35.4 g, 0.563 mmol) was added to the reaction mixture, stirred for 18 hours, quenched with sat. NaHCO3 and extracted with ethyl acetate. The organic phase was concentrated in vacuo. Purification by flash chromatography (silica, 2:8 EtOAc:hexanes) provided the title compound (43.6 g, 39.8% yield) as a solid.

후처리

  1. stirringstirred for 30 minutes
  2. stirringstirred for 18 hours
  3. customquenched with sat. NaHCO3
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic phase was concentrated in vacuo
  6. customPurification by flash chromatography (silica, 2:8 EtOAc:hexanes)

출처 및 근거

ORD 기록
ord-ef2c1d09dd4d43028376f0050abfad40
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671043B2

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