Hydrochloric Acid → HCID 513971, compound
Reaction equation
C(OC(=O)[NH:7][C@H:8]([C:20](=[O:44])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][C@H:26]([N:29]([S:34]([C:37]1[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=1)(=[O:36])=[O:35])[CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:27][OH:28])[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(C)(C)C.Cl>C(O)C>[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[C:20]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][C@H:26]([N:29]([S:34]([C:37]1[CH:38]=[CH:39][C:40]([NH2:43])=[CH:41][CH:42]=1)(=[O:36])=[O:35])[CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:27][OH:28])=[O:44]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(1S,5S)-(1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-naphthalen-2-yl-ethyl)-carbamic acid tert-butyl ester (698 mg, 1.089 mmol) was added to 6 mL of ethanol and 6 mL of HCl. The mixture was stirred at room temperature until completion by TLC. The ethanol was evaporated and the acidic mixture was poured into an extracting funnel containing 75 mL of ethyl acetate and 50 mL of HCl 1M and separated. The aqueous layer was washed with ethyl acetate. The aqueous phase was basified with pellets of NaOH and poured into an extracting funnel. The organic layer was washed with NaOH 1M and brine, dried over sodium sulfate, filtered, evaporated and dried under vacuum to give 544 mg (92%) of a yellow solid (Rf=0, 100% EtOAc, indicator: ninhydrin).