Diethylcarbamoyl chloride → HCID 69280839, compound
Reaction equation
[N:1]1([C:5]2[S:6][C@H:7]3[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[C@H:10]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C@H:8]3[N:9]=2)[CH2:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:46]([N:48]([CH2:52][CH3:53])[C:49](Cl)=[O:50])[CH3:47]>C1COCC1>[CH2:46]([N:48]([CH2:52][CH3:53])[C:49](=[O:50])[O:15][CH2:14][C@H:12]1[O:13][C@H:7]2[C@H:8]([N:9]=[C:5]([N:1]3[CH2:4][CH2:3][CH2:2]3)[S:6]2)[C@@H:10]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[C@@H:11]1[O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[CH3:47]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ((3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methanol (300 mg, 0.60 mmol) in THF (10 mL) was added NaHMDS (1.1 g, 6.01 mmol), and followed by addition of diethylcarbamic chloride (1.22 g, 9.04 mmol) at room temperature. After stirring for 1 h, the reaction mixture was quenched with saturated aqueous NH4Cl (50 mL), extracted with dichloromethane (3×30 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give a crude product 7 (320 mg), which was used in next step directly without further purification. [M+H]+ 600.1
Workup
- customthe reaction mixture was quenched with saturated aqueous NH4Cl (50 mL)
- extractionextracted with dichloromethane (3×30 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-dbdb00f5ee884d0cb03e341d885da505
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933040B2
Reaction notes
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