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Triphenylphosphine → Ethyl [(4-{[1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethyl]thio}-2-methylphenyl)oxy]acetate

HRID 1391799
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HRID 1391799 반응식
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:15])[CH:3]=1.[Br:16][C:17]1[N:22]=[C:21]([CH:23](O)[CH2:24][O:25][CH2:26][CH3:27])[CH:20]=[CH:19][CH:18]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[Br:16][C:17]1[N:22]=[C:21]([CH:23]([S:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:15])[CH:3]=2)[CH2:24][O:25][CH2:26][CH3:27])[CH:20]=[CH:19][CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetateHCID 586298281-(6-Bromo-2-pyridinyl)-2-(ethyloxy)ethanol

생성물 1

HCID 58629945Ethyl [(4-{[1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethyl]thio}-2-methylphenyl)oxy]acetate

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

A solution of (ethyl [(4-mercapto-2-methylphenyl)oxy]acetate) (386 mg, 1.71 mmol), 1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethanol (352 mg, 1.43 mmol) and PPh3 (450 mg, 1.72 mmol) in DCM (17 mL) at 0° C. under nitrogen was stirred for 10 mins and then treated drop-wise with DIAD (0.34 mL, 1.73 mmol). The resulting mixture was then stirred, with slow warming to ambient temperature over 18 h. The mixture was then reduced under vacuum and the resulting yellow oil purified by SPE (silica, 20 g cartridge), eluting with cyclohexane:EtOAc (gradient 15:1 to 5:1). Further purification using the OPTIX-SPE (C18 cartridge, 50 g) eluting with 60-80% MeCN (+0.05% HCOOH) in H2O (+0.01% HCOOH) over 56 mins afforded the title compound as an oil (232 mg).

후처리

  1. customthe resulting yellow oil purified by SPE (silica, 20 g cartridge)
  2. washeluting with cyclohexane
  3. customFurther purification
  4. washeluting with 60-80% MeCN (+0.05% HCOOH) in H2O (+0.01% HCOOH) over 56 mins

출처 및 근거

ORD 기록
ord-baea51d241ba4cbf8d526c58ea1d4d10
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07338960B2

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