Sodium Hydroxide → N-{2(S)-[4-(4-nitrophenyl)butanoylamino]-3(S)-methylpentyl}-N-(1-naphthylmethyl)-glycyl-methionine
Reaction equation
C[O:2][C:3](=[O:46])[C@H:4]([CH2:42][CH2:43][S:44][CH3:45])[NH:5][C:6](=[O:41])[CH2:7][N:8]([CH2:20][C@@H:21]([NH:26][C:27](=[O:40])[CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)[C@@H:22]([CH3:25])[CH2:23][CH3:24])[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>CO>[N+:37]([C:34]1[CH:35]=[CH:36][C:31]([CH2:30][CH2:29][CH2:28][C:27]([NH:26][C@@H:21]([C@@H:22]([CH3:25])[CH2:23][CH3:24])[CH2:20][N:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:7][C:6]([NH:5][C@H:4]([C:3]([OH:46])=[O:2])[CH2:42][CH2:43][S:44][CH3:45])=[O:41])=[O:40])=[CH:32][CH:33]=1)([O-:39])=[O:38]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
The methyl ester from Step F (87 mg, 130 μmol) was dissolved in MeOH (1 ml) and 1.00N NaOH (300 μl, 300 μmol) was added. The mixture was stirred at 45° C. under argon for 45 minutes, then the solution was partitioned between EtOAc (100 ml) and 5% citric acid (50 ml). The organic layer was washed with H2O (2×50 ml), dried (MgSO4), filtered and evaporated to give the title compound.
Workup
- customthe solution was partitioned between EtOAc (100 ml) and 5% citric acid (50 ml)
- washThe organic layer was washed with H2O (2×50 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-22e32e0de07649a78d16364edc56c750
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05523456
Reaction notes
Loading…