Dimethylformamide → HCID 10549647, compound
Reaction equation
[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][CH:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:24](=O)[NH:23][CH:22]=[N:21][C:20]1=2)(=[O:3])[CH3:2].CN(C=O)C.C(Cl)[Cl:35]>>[Cl:35][C:24]1[N:23]=[CH:22][N:21]=[C:20]2[C:25]=1[N:26]=[CH:27][N:19]2[C@@H:6]1[O:7][C@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:5]1[O:4][C:1](=[O:3])[CH3:2]Participants
4
Conditions
- Temperature
- 55 °C
Procedure
Crude compound 2 (130 mg) was dissolved in dry CH2Cl2 (10 mL) and heated to 55° C. Dry DMF (1 mL) followed by a 2 M solution of SOCK in CH3Cl2 (2.43 mL, 0.57 mmol) were added dropwise over a period of 45 minutes. The reaction mixture was gently refluxed for an additional 75 minutes. The reaction mixture was cooled to room temperature and diluted with CH2Cl2. The organic layer was washed with saturated NaHCO3 solution (2×50 mL), brine (50 mL) and dried (anhydrous sodium sulfate). The organic phase was concentrated in vacuo and purified by preparative TLC (5% MeOH/CHCl3) to obtain pure 3 (50 mg, 26% from 1): UV (MeOH)λmax 263.0 nm, 212.5 nm.
Workup
- additionwere added dropwise over a period of 45 minutes
- temperatureThe reaction mixture was gently refluxed for an additional 75 minutes
- temperatureThe reaction mixture was cooled to room temperature
- washThe organic layer was washed with saturated NaHCO3 solution (2×50 mL), brine (50 mL)
- dry with materialdried (anhydrous sodium sulfate)
- concentrationThe organic phase was concentrated in vacuo
- custompurified by preparative TLC (5% MeOH/CHCl3)
- customto obtain pure 3 (50 mg, 26% from 1)
Sources & evidence
- ORD record
- ord-5f033cc7bba74cb1a4146b49785c6f98
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271212B1
Reaction notes
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