Methanol → (4-Amino-butyl)-(4-tert-butoxycarbonylamino-butyl)-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of (4-Amino-butyl)-(4-tert-butoxycarbonylamino-butyl)-carbamic acid tert-butyl ester 12 (460 mg, 1.28 mmol) and CH2Cl2 (3 mL) was prepared. Note: 12 is a known compound (ref: “Total Synthesis of Petrobactin and Its Homologues as Potential Growth Stimuli for Marinobacter hydrocarbonoclasticus, an oil-degrading bacteria.” Gardner, R. A.; Kinkade, R.+; Wang, C.; Phanstiel IV, O. J. Org. Chem. 2004, 69, 3530-3537). A solution of K2CO3 (420 mg, 3.04 mmol) and water (5 mL) was added to the original mixture. Aliquat (0.10 mL) was added and the mixture was cooled to 0° C. 1,3,5-benzenetricarboxylic acid chloride 11 (105 mg, 0.395 mmol) in CH2Cl2 (6 mL) was added dropwise to the original mixture and allowed to gradually warm and stir vigorously at rt for 6 hours. TLC (95% CH2Cl2, 4% MeOH, 1% NH4OH Rf=0.35) was used to monitor the reaction. After the reaction was complete, the aqueous layer was extracted three times in CH2Cl2 and saturated Na2CO3. The organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated to give 590 mg of crude product. The crude was subjected to flash column chromatography (95% CH2Cl2, 4% MeOH, 1% NH4OH Rf=0.35) to give 13 (382 mg, 0.310 mmol, 78%). 1H NMR (CDCl3): δ 8.41 (s, 3H), 4.75 (br s, 3H), 3.49 (m, 6H), 3.23-3.06 (m, 18H), 2.78-1.30 (m, 78H).

Provenance & Evidence