Hydrochloric Acid → HCID 131720753, compound
Reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=O)[CH2:3]C1C=CC=CC=1.C[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.ClC([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])=O.Cl.[NH2:29][C@@H:30]([CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33].Cl.[CH2:50]1[CH2:54]OC[CH2:51]1>>[N:14]1([C:24]([C:25]2[CH:26]=[CH:54][C:50]([NH:1][C@H:2]([C:10]([NH:29][C@@H:30]([CH2:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:31][S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)(=[O:34])=[O:33])=[O:12])[CH3:3])=[CH:51][CH:27]=2)=[O:23])[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1Participants
7
Procedure
To a solution of Mu-PheOH (0.342 g, 1.23 mmol) in THF (10 mL) at -10° C. were added 4-methylmorpholine (0.135 mL, 1.23 mmol) and isobutyl chloroformate (0.159 mL, 1.23 mmol). The mixture was stirred for 10 minutes, whereupon (S)-2-amino-4-phenyl-1-phenylsulfonylbutane hydrochloride (0.40 g, 1.23 mmol) was added, followed by 4-methylmorpholine (0.135 mL, 1.23 mmol). The mixture was stirred for 45 minutes. 1M HCl (15 mL) was added. The product was extracted with ethyl acetate (30 mL), washed with saturated aqueous sodium bicarbonate (15 mL), brine (15 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The final product, Mu-Phe-Hph-β-SO2Ph, weighed 0.68 g (100% yield).
Workup
- additionwas added
- extractionThe product was extracted with ethyl acetate (30 mL)
- washwashed with saturated aqueous sodium bicarbonate (15 mL), brine (15 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-ce4f87c40431405dbf0e9f230c5f94ae
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05776718
Reaction notes
Loading…