(12S,15R)-benzyl 12-(tert-butoxycarbonylamino)-8-(2-(tert-butoxycarbonylamino)ethyl)-2,2-dimethyl-4,9,13-trioxo-15-(4-(trifluoromethyl)benzyl)-3-oxa-5,8,14-triazahexadecan-16-oate → (12S,15R)-12-(tert-butoxycarbonylamino)-8-(2-(tert-butoxycarbonylamino)ethyl)-2,2-dimethyl-4,9,13-trioxo-15-(4-(trifluoromethyl)benzyl)-3-oxa-5,8,14-triazahexadecan-16-oic acid

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Reaction Steps

To a solution of (12S,15R)-benzyl 12-(tert-butoxycarbonylamino)-8-(2-(tert-butoxycarbonylamino)ethyl)-2,2-dimethyl-4,9,13-trioxo-15-(4-(trifluoromethyl)benzyl)-3-oxa-5,8,14-triazahexadecan-16-oate (3 g, 3.58 mmol) in a mixture of EtOH/H2O (18 mL/2 mL) was added palladium (wet) on carbon (catalytic amount). The reaction mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The catalyst was filtered through a pad of Celite. The filtrate was evaporated under reduced pressure to give (12S,15R)-12-(tert-butoxycarbonylamino)-8-(2-(tert-butoxycarbonylamino)ethyl)-2,2-dimethyl-4,9,13-trioxo-15-(4-(trifluoromethyl)benzyl)-3-oxa-5,8,14-triazahexadecan-16-oic acid (CLXVI) as white crystals (2.66 g, 3.56 mmol, 99% yield). 1H NMR (DMSO-d6) δ ppm 1.32 (s, 27H), 1.52-1.78 (m, 2H), 2.07-2.26 (m, 2H), 2.9-3.03 (m, 4H), 3.14-3.23 (m, 4H), 3.31 (brs, 2H), 3.83-3.92 (m, 1H), 4.4-4.46 (m, 1H), 6.74-6.85 (m, 2H), 6.88-6.94 (m, 1H), 7.38 (d, J=8 Hz, 2H), 7.55 (d, J=8 Hz, 2H), 7.94-8.01 (m, 1H); 19F NMR (DMSO-d6) δ ppm −60.24 (s, 3F); ESIMS found for C34H52F3N5O10 m/z 748.9 (M+H).

Provenance & Evidence