(S)-(-)-Lactamide → HCID 86717529, compound
Reaction equation
[OH:1][C@@H:2]([CH3:6])[C:3](N)=O.F[B-](F)(F)F.C([O+](CC)CC)C.[NH2:19][C:20]1[C:21]([NH:29][C@@H:30]2[CH2:35][O:34][C@@H:33]([CH2:36][OH:37])[CH2:32][CH2:31]2)=[C:22]2[S:28][CH:27]=[CH:26][C:23]2=[N:24][CH:25]=1>C1COCC1.C(O)C.CO>[OH:37][CH2:36][C@@H:33]1[O:34][CH2:35][C@@H:30]([N:29]2[C:21]3=[C:22]4[S:28][CH:27]=[CH:26][C:23]4=[N:24][CH:25]=[C:20]3[N:19]=[C:3]2[C@@H:2]([OH:1])[CH3:6])[CH2:31][CH2:32]1Participants
Procedure
A mixture of (2S)-2-hydroxypropanamide (86.6 mg, 0.972 mmol) and triethyloxonium tetrafluoroborate (185 mg, 0.972 mmol) in THF (2 mL) was stirred at room temperature for 2 h. The solvent was removed and the residue dissolved in ethanol (0.50 mL) and added to a suspension of {(2R,5S)-5-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]tetrahydro-2H-pyran-2-yl}methanol (65.0 mg, 0.233 mmol) in ethanol (1.8 mL). The mixture was stirred at 80° C. for 1 h. The mixture was cooled to room temperature, diluted with methanol, and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product as white solid (45 mg, 58%). LCMS calculated for C16H20N3O3S (M+H)+: m/z=334.1. Found: 334.
Workup
- customThe solvent was removed
- dissolutionthe residue dissolved in ethanol (0.50 mL)
- stirringThe mixture was stirred at 80° C. for 1 h
- temperatureThe mixture was cooled to room temperature
- custompurified with prep-LCMS (XBridge C18 column
- washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)
Sources & evidence
- ORD record
- ord-9f401e17b267446e9b682a0297cba2c1
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181271B2
Reaction notes
Loading…