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

HRID 1013512Notes

Reaction equation

HRID 1013512 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-4e9c38c08bdd468ca3774727bdc07dca
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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