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

HRID 1013512ノート

反応式

HRID 1013512 の反応式
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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-4e9c38c08bdd468ca3774727bdc07dca
出典データセット
uspto-grants-2011_07
特許番号
US07981874B2

反応ノート

読み込み中…