Cyclopropanecarbonyl chloride → HCID 58565224, compound

HRID 554597Notes

Reaction equation

HRID 554597 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH2:12][NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=1)[CH3:2].C(N(C(C)C)CC)(C)C.[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH2:12][N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:34]([CH:31]2[CH2:33][CH2:32]2)=[O:35])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 58565161HCID 58565161, compound

Product 1

HCID 58565224HCID 58565224, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Benzylamino-methyl)-4-bromo-benzoic acid ethyl ester (5.0 g, 12.9 mmol) and diisopropylethylamine (6.7 mL, 38.7 mmol) were combined in CH2Cl2 (100 mL) at room temperature. Cyclopropanecarbonyl chloride (1.77 mL, 19.4 mmol) was added dropwise, and the reaction was stirred at room temperature until no starting material was seen by analytical LCMS. The mixture was worked-up and purified by silica gel chromatography to give 3-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-bromo-benzoic acid ethyl ester.

Workup

  1. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-868a6040250a47f6bca25da32e551ee0
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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