Potassium Carbonate → HCID 44595801, compound
Reaction equation
[OH:1][CH2:2][C@@H:3]([NH:7][C:8]([C:10]1[N:11]=[N:12][C:13]([C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[C@@H:24]([CH:29]([CH2:31][CH3:32])[CH3:30])[CH2:23]2)=[O:21])=[CH:14][C:15]=1[CH2:16][CH:17]([CH3:19])[CH3:18])=O)[CH:4]([CH3:6])[CH3:5].CCN(S(F)(F)F)CC.C([O-])([O-])=O.[K+].[K+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:29]([C@@H:24]1[N:25]([CH3:28])[CH2:26][CH2:27][N:22]([C:20]([C:13]2[N:12]=[N:11][C:10]([C:8]3[O:1][CH2:2][C@H:3]([CH:4]([CH3:5])[CH3:6])[N:7]=3)=[C:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[CH:14]=2)=[O:21])[CH2:23]1)([CH2:31][CH3:32])[CH3:30]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
β-Hydroxy amide 16 (8 mg, 0.018 mmol) was dissolved in 500 μL DCM and cooled to −78° C. DAST (3 μL, 0.020 mmol, 3.2 mg) was added slowly and the reaction mixture was stirred for 1 hour at −78° C. The reaction was quenched with the addition of ca. 4 mg K2CO3 (0.027 mmol) and allowed to warm to room temperature. Saturated sodium bicarbonate was added (1 mL), the product was extracted with DCM (3×1 mL), washed with brine (1×1 mL), dried over magnesium sulfate and evaporated to give a yellow oil. The product was purified by prep plate chromatography (250 μm×20 cm×20 cm; 9.8:0.2:0.1% DCM-MeOH-Et3N, Rf=0.20) to give 5 mg (65%) of a colorless oil.
Workup
- temperatureto warm to room temperature
- extractionthe product was extracted with DCM (3×1 mL)
- washwashed with brine (1×1 mL)
- dry with materialdried over magnesium sulfate
- customevaporated
- customto give a yellow oil
- customThe product was purified by prep plate chromatography (250 μm×20 cm×20 cm; 9.8:0.2:0.1% DCM-MeOH-Et3N, Rf=0.20)
Sources & evidence
- ORD record
- ord-99cebe409812471f896955853d0efbf4
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07579350B2
Reaction notes
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