HCID 10316106, compound → HCID 9837054, compound
Reaction equation
[O:1]=[C:2]1[C:6]([CH2:7][C@H:8]([NH:16]C(OC(C)(C)C)=O)[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:5][C:4](=[O:24])[N:3]1[CH3:25]>C(C(O)=O)(F)(F)F>[O:1]=[C:2]1[C:6]([CH2:7][C@H:8]([NH2:16])[C:9]([OH:11])=[O:10])=[CH:5][C:4](=[O:24])[N:3]1[CH3:25]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound 12 (1 g, 2.8 mmol) was dissolved in CF3CO2H (20 mL) which had been precooled in an ice bath. This mixture was stirred overnight at room temperature. The acid was removed under vacuum and the residue dried under high vacuum overnight. This residue was dissolved in water (1 mL) and subjected to cation-exchange chromatography (AG 50W-X8, column volume=3 mL). The column was eluted with water, and the fractions corresponding to product were evaporated to dryness. The residue was dissolved in a small amount of water and lyophilized to give 0.33 g (59%) of 3 as a white solid: mp 190°-194° C. dec; [α]D +2.5° (c 0.28, H2O); 1H NMR (300 MHz, D2O) δ 2.9 (s, 3 H, CH3), 2.96-3.0 (m, 2 H, CH2), 3.97 (dd, J=6.41 and 7.02 Hz 1 H α-CH ) 6.6 (m, 1 H, C=CH ); 13C NMR (75 MHz, D2O) δ 23.53 (CH3), 26.57 (CH2), 52.96 (α-C), 130.07 (C=C), 143.79 (C=C), 172.59 (C=O), 172.72 (C=O), 173.01 (C=O). FAB-MS m/z 199 (MH)+. Anal. (C8H10N2O4.1/3H2O) C, H, N.
Workup
- customhad been precooled in an ice bath
- customThe acid was removed under vacuum
- customthe residue dried under high vacuum overnight
- dissolutionThis residue was dissolved in water (1 mL)
- washThe column was eluted with water
- customthe fractions corresponding to product were evaporated to dryness
- dissolutionThe residue was dissolved in a small amount of water
Sources & evidence
- ORD record
- ord-185c8a9a5e5d43748fa63bb180a75f81
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05359087
Reaction notes
Loading…