Hydrochloric Acid → HCID 22619641, compound

Participants

Reaction Steps

A mixture of 32 mg (0.212 mmol) of 4-(aminomethyl)benzoic acid in 2 ml of H2O and 4 ml of THF was treated with approximately 0.1 ml of 2 N NaOH such that the pH of the mixture was about 9. This was then treated with a solution of 100 mg (0.209 mmol) of the TCA NHS ester 9 in 4.5 ml of THF. The pH was adjusted to about 8.5-9.0 with 2 N NaOH and the reaction was stirred at room temperature for 15 minutes. The reaction was neutralized to pH 6 with 2 N HCl, then extracted twice with CH2Cl2. The CH2Cl2 portions were combined, dried over anhydrous Na2SO4 and concentrated in vacuo to give 87 mg (81%) of the acid 15 as a pale yellow oil. This was used in the next step without further purification.

Provenance & Evidence