Stannous chloride dihydrate → HCID 70012413, compound
Reaction equation
[OH:1][C@@H:2]([C@@H:21]([NH:29][C:30]([O:32][C@H:33]1[CH2:38][CH2:37][CH2:36][O:35][CH2:34]1)=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:3]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[NH:4][CH2:5][CH:6]([CH3:8])[CH3:7].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[OH:1][C@@H:2]([C@@H:21]([NH:29][C:30]([O:32][C@H:33]1[CH2:38][CH2:37][CH2:36][O:35][CH2:34]1)=[O:31])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH:3]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[NH:4][CH2:5][CH:6]([CH3:8])[CH3:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 2(S)-hydroxy-3(S)-[3(S)-tetrahydropyranyloxycarbonyl]amino-1-(4-nitrobenzenesulfonyl)-1-isobutylamino-4-phenylbutane (36 mg, 0.067 mmol) and SnCl2.2H2O (77 mg, 0.34 mmol) in 1 mL of EtOAc was heated to 70° C. After 1 h the starting material disappeared and the solution was allowed to cool to room temperature. The mixture was poured into sat aq NaHCO3 solution (3 mL) and extracted with EtOAc (10 mL). The organic extract was dried over anhyd MgSO4 and concentrated under reduced pressure to give 30 mg of 2(S)-hydroxy-3(S)-[3(S)-tetrahydropyranyloxycarbonyl]amino-1-(4-aminobenzenesulfonyl)-1-isobutylamino-4-phenylbutane.
Workup
- temperatureto cool to room temperature
- additionThe mixture was poured
- extractionextracted with EtOAc (10 mL)
- extractionThe organic extract
- dry with materialwas dried over anhyd MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-1b30ce9d4e0049a28e2cbab72f7079e7
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06573388B1
Reaction notes
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