1-Heptanethiol → 4-[1-Phenyl-1-(5-(azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester

HRID 606763

반응식

HRID 606763 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:15]2[O:16][C:17]([CH:20]3[CH2:23][N:22](C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH2:21]3)=[N:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(S)CCCCCC>C1COCC1.C1CCN2C(=NCCC2)CC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:15]2[O:16][C:17]([CH:20]3[CH2:21][NH:22][CH2:23]3)=[N:18][N:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 154221-HeptanethiolHCID 670463744-[1-Phenyl-1-(5-(N-(9-fluorenylmethoxycarbonyl)azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 670464414-[1-Phenyl-1-(5-(azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester수율 74.7%

시약·촉매·용매 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-[1-phenyl-1-(5-(N-(9-fluorenylmethoxycarbonyl)azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester (0.161 g, 0.260 mmol) and heptanethiol (0.398 mL, 2.60 mmol) in THF (2.6 mL) at rt was added DBU (2 drops). The mixture was allowed to stir for 18 h and then the solvent was removed in vacuo. The residue was dissolved in MeOH and purified by preparative HPLC(NH4OAc) to afford the title compound (0.077 g, 74%) as a colorless solid:

후처리

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in MeOH
  3. custompurified by preparative HPLC(NH4OAc)

출처 및 근거

ORD 기록
ord-f07e2eb3b3584e88a06d480a4bf456e3
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915283B2

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