Methanol → HCID 178494117, compound
Reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15](SC(C)C)[N:14]=3)=[C:11]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:10]=[CH:9]2)[CH2:4][CH2:3]1.OOS([O-])=O.[K+].[CH3:36][OH:37]>>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([O:37][CH3:36])[N:14]=3)=[C:11]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[N:10]=[CH:9]2)[CH2:4][CH2:3]1Participants
Procedure
The product of step (b) above, (10.8 g, 26.2 mmol) was dissolved in 43 mL of MeOH and Oxone™ (12.1 g, 19.6 mmol) was added and the resulting suspension was stirred at room temperature for 4-24 h. After HPLC confirmed that no starting material remained, the remaining Oxone™ salts were removed by filtration of the suspension through a Buchner funnel. A NaOMe/MeOH solution (25%, 16 mL) was added to the solution until the pH was about 12. After 20 min, HPLC confirmed that the reaction was complete and 100 mL of water was added to the reaction. The resulting solution was stirred at room temperature for 3 h, then filtered through a Buchner funnel and rinsed with 50 mL of water. The pale white solid was dried in the vacuum oven at 65° C. for 18 h to yield 6.0 h (62% yield) of title compound.
Workup
- customthe remaining Oxone™ salts were removed by filtration of the suspension through a Buchner funnel
- additionA NaOMe/MeOH solution (25%, 16 mL) was added to the solution until the pH was about 12
- waitAfter 20 min
- addition100 mL of water was added to the reaction
- stirringThe resulting solution was stirred at room temperature for 3 h
- filtrationfiltered through a Buchner funnel
- washrinsed with 50 mL of water
- customThe pale white solid was dried in the vacuum oven at 65° C. for 18 h
Sources & evidence
- ORD record
- ord-be20fcb236004f6aa40a9bfd7083a7af
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06329526B1
Reaction notes
Loading…