2,4-Dichlorobenzoic Acid → HCID 57798315, compound

HRID 2100303Notes

Reaction equation

HRID 2100303 reaction equation
[NH2:1][C@H:2]([C:4]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1)[CH3:3].[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:23]=1[C:24]([NH:1][C@H:2]([C:4]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:5][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7]1)[CH3:3])=[O:25]

Participants

5

Reactant 3

HCID 57872,4-Dichlorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 57798316HCID 57798316, compound

Product 1

HCID 57798315HCID 57798315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-[(1S)-1-aminoethyl]-3-pyridin-2-ylazetidine-1-carboxylate (I-3, 1.35 g, 5.1 mmol) in CH2Cl2 (11 mL) was treated with 2,4-dichlorobenzoic acid (1.2 g, 6.1 mmol) EDCI (2.0 g, 10.2 mmol), and HOBt (690 mg, 5.1 mmol) and stirred at room temperature. After 18 h, the reaction was quenched with the addition of H2O (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried (Na2SO4), concentrated under reduced pressure, and purified by flash chromatography (120 g SiO2, 50-80% EtOAc/hexanes) to afford tert-butyl 3-{(1S)-1-[(2,4-dichlorobenzoyl)amino]ethyl}-3-pyridin-2-ylazetidine-1-carboxylate (I-4). Analytical LCMS: single peak (214 nm), 3.010 min. This material was used in subsequent reactions without further purification.

Workup

  1. customthe reaction was quenched with the addition of H2O (50 mL)
  2. extractionextracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash chromatography (120 g SiO2, 50-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6eeb31e77790485fa9051aa9f0ff7f45
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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