Water → Tert-butyl 4-(2-chloro-5-nitrophenylsulfonyl)piperazine-1-carboxylate

HRID 244363노트

반응식

HRID 244363 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CCOC(C)=O.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([N:18]1[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]1)(=[O:13])=[O:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 206302-Chloro-5-nitrobenzenesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

생성물 1

HCID 59260816Tert-butyl 4-(2-chloro-5-nitrophenylsulfonyl)piperazine-1-carboxylate수율 83.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of compound 37 (0.600 g, 2.34 mmol) in DCM (20.00 mL) was added tert-butyl 1-piperazinecarboxylate (0.566 g, 3.04 mmol) and TEA (0.422 mL, 3.04 mmol). The reaction was monitored with TLC (25% EtOAc in hexanes, Rf=0.53). The reaction mixture was complete after stirring at room temperature for 1 hr, as indicated by the absence of the starting material (TLC). Water was added and aqueous layer was extracted twice with DCM. Combined extracts were sequentially washed with water and brine, dried over MgSO4, filtered, and evaporated in vacuo to afford a yellow solid. The solid was triturated with DCM and hexanes, and then filtered to yield compound 38 as a yellow solid (0.789 g, 100% HPLC purity, 83% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.60 (d, J=3 Hz, 1H), 8.47 (dd, J1=3 Hz, J2=8 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 3.37 (m, 4H), 3.23 (m, 4H), 1.37 (s, 9H).

후처리

  1. extractionaqueous layer was extracted twice with DCM
  2. washCombined extracts were sequentially washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a yellow solid
  7. customThe solid was triturated with DCM and hexanes
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-078429561bef4952be1dfa8c2e9147db
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658642B2

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