Hydrochloric Acid → HCID 59828864、化合物

反応式

C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([CH:20]2[CH2:22][CH2:21]2)=[O:19])=[CH:12][CH:11]=1)=O)(C)(C)C.Cl>CCOC(C)=O.CO>[CH:20]1([C:18]([NH:17][CH2:16][C:13]2[CH:12]=[CH:11][C:10]([CH2:9][NH2:8])=[CH:15][CH:14]=2)=[O:19])[CH2:21][CH2:22]1

参加物

実験手順

Dissolve N-(tert-butoxycarbonyl)-4-[(cyclopropanecarbonyl-amino)-methyl]-benzylamine (529 mg, 1.74 mmol) in EtOAc (20 mL) and MeOH (15 mL). Bubble hydrogen chloride through the solution for 15 min, and stir the mixture overnight at room temperature. Concentrate the mixture in vacuo and dissolve the resulting solid in water. Adjust the pH to 9-11 with 20% aqueous K2CO3 (w/w %) and extract three times with chloroform/iso-propanol (3:1). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (40 g, pre-packed cartridge) eluting with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 4:1 over 5 min, 1:1 over 10 min, 1:3; 50 mL/min) to obtain the desired intermediate (275 mg, 77%). MS (APCI+) m/z: 188 (M-NH3+H)+.