Water → N-[5-[(1R)-1,2-Dihydroxyethyl]-2-pyridinyl]acetamide
Reaction equation
C([OH:5])(C)(C)C.[CH:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[N:12][CH:13]=1)=[CH2:7].S([O-])([O-])=O.[Na+].[Na+].[OH2:24]>CC(O)C>[OH:24][C@H:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[N:12][CH:13]=1)[CH2:7][OH:5]Participants
Conditions
- Temperature
- 5 °C
Procedure
A suspension of AD-Mix-B® (56.33 g) in water (200 ml) and t-butanol (200 ml) was cooled to 5° C. and N-(5-Vinyl-pyridin-2-yl)-acetamide (6.52 g, 40.2 mmol) was added followed by 2-propanol (400 ml). The mixture was stirred at 5° C. for 12 hours and then at 20 ° C. for 12 hours. The reaction mixture was then treated with sodium sulfite (60.4 g), stirred for 30 minutes and then diluted with 500 ml of 2-propanol and stirred for an additional one hour. The mixture was filtered and the alcoholic phase was separated and evaporated to dryness. The residue was slurried in 500 ml of 2-propanol and evaporated again. The residue was dried to afford 6.35 g (80%) of the title product as colorless crystals. The crystals were recrystallized by dissolving in hot glacial acetic acid, diluting 7-fold with 2-propanol, cooling and seeding to give the title product as crystals. mp 184-185° C. 1H NMR (dmso-d6): δ=8.22 (d, 1 H); 7.99 (d, 1 H); 7.68 (d of d, 1 H); 4.52 (t, 1 H); 3.44 (m, 2 H); 2.07 (s, 3 H). MS (Cl): m/z=197 (M+H+). Optical Rotation: -4.52° (c=0.05, acetic acid). Analysis: Calculated for C9H12N2O3 : C, 55.09%; H,6.17%; N, 14.28%. Found: C, 55.43%; H, 5.97%; N,13.96%.
Workup
- waitat 20 ° C. for 12 hours
- stirringstirred for 30 minutes
- stirringstirred for an additional one hour
- filtrationThe mixture was filtered
- customthe alcoholic phase was separated
- customevaporated to dryness
- customevaporated again
- customThe residue was dried
Sources & evidence
- ORD record
- ord-024cb80f3714463787505b8d4dd9e3e5
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06001856
Reaction notes
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