Triethylamine chloroform → Benzoyl chloride

HRID 2181168Notes

Reaction equation

C(N(CC)CC)C.C(Cl)(Cl)[Cl:9].C[O:13][C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1NC(=O)CC1C=CC(OC2C=CC(O[C@H]3CC[C@@H](N)CC3)=CC=2)=CC=1>>[C:14]([Cl:9])(=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 18929042Triethylamine chloroform

HCID 178497647HCID 178497647, compound

Product 1

HCID 7412Benzoyl chlorideYield 149.1%

Procedure

A reactor was charged with 358 μl (1.7 eq, 179 μmol) of 0.5M triethylamine-chloroform solution containing 420 μl (105 μmol, 50 mg) of 2-(2-(4-(4-(cis-4-aminocyclohexyloxy)phenoxy)phenyl)acetylamino)benzoic acid methyl ester (0.25M-CHCl3) obtained by the Example 17, benzoyl chloride (1.5 eq, 22 mg) was added thereto and the mixture was stirred for 2.5 hours. After completing the reaction, 139 mg (157.5 μmol) of an aminomethylated polystyrene resin (product of Novabiochem) was added to the system and stirred for 12 hours. The solution was put on a Silica cartridge (product of Waters) and developed with a hexane/ethyl acetate mixture (1/2) and the obtained solution was distilled to remove the solvent.

Sources & evidence

ORD record: ord-460ffced0da741588ce93ed19f2ada17
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890932B2

Reaction notes

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