1,2-Dichloroethane → tert-Butyl 4-[2-(4-ethyl-4-oxido-1,4-azaphosphinan-1-yl)-2-oxoethyl]benzoate

HRID 1013512노트

반응식

HRID 1013512 반응식
Cl.[CH2:2]([P:4]1(=[O:10])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)[CH3:3].[C:11]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](O)=[O:26])=[CH:20][CH:19]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH2:2]([P:4]1(=[O:10])[CH2:9][CH2:8][N:7]([C:25](=[O:26])[CH2:24][C:21]2[CH:20]=[CH:19][C:18]([C:16]([O:15][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:17])=[CH:23][CH:22]=2)[CH2:6][CH2:5]1)[CH3:3]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 598545182-(4-(Tert-butoxycarbonyl)phenyl)acetic acidHCID 673168024-Ethyl-1,4lambda5-azaphosphinan-4-one hydrochloride

생성물 1

HCID 57925996tert-Butyl 4-[2-(4-ethyl-4-oxido-1,4-azaphosphinan-1-yl)-2-oxoethyl]benzoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

4-Ethyl-1,4-azaphosphinane 4-oxide hydrochloride (233 mg, 1.27 mmol), [4-(tert-butoxycarbonyl)phenyl]acetic acid (200 mg, 0.847 mmol), EDC (325 mg, 1.69 mmol), HOBT (259 mg, 1.69 mmol), and DIEA (296 μl, 1.69 mmol) were combined in DMF (4 mL) and stirred at room temperature overnight. The solution was diluted with saturated NaHCO3 and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/CH2Cl2) afforded the title compound as a colorless oil. MS: cal'd 366 (MH+), exp 366 (MH+).

후처리

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

출처 및 근거

ORD 기록
ord-4e9c38c08bdd468ca3774727bdc07dca
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981874B2

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