Lithium Hydroxide → HCID 73776348, compound

HRID 712005Notes

Reaction equation

HRID 712005 reaction equation
[OH:1][C@H:2]([CH3:6])[C:3](N)=O.F[B-](F)(F)F.C([O+](CC)CC)C.C([O:22][CH2:23][CH:24]1[CH2:29][CH2:28][C@H:27]([NH:30][C:31]2[C:36]([NH2:37])=[CH:35][N:34]=[C:33]3[CH:38]=[CH:39][S:40][C:32]=23)[CH2:26][O:25]1)(=O)C.[OH-].[Li+]>C1COCC1.C(O)C.O.CO>[OH:22][CH2:23][CH:24]1[O:25][CH2:26][C@@H:27]([N:30]2[C:31]3=[C:32]4[S:40][CH:39]=[CH:38][C:33]4=[N:34][CH:35]=[C:36]3[N:37]=[C:3]2[C@H:2]([OH:1])[CH3:6])[CH2:28][CH2:29]1

Participants

9

Reactant 4

HCID 3939Lithium HydroxideHCID 1530236(2R)-2-hydroxypropanamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 86717464HCID 86717464, compound

Product 1

HCID 73776348HCID 73776348, compoundYield 63.2%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-2-hydroxypropanamide (131 mg, 1.47 mmol) and triethyloxonium tetrafluoroborate (263 mg, 1.38 mmol) in THF (2 mL) was stirred at room temperature for 2 h. The solvent was removed and the residue dissolved in ethanol (0.85 mL) and added to a suspension of {(5S)-5-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]tetrahydro-2H-pyran-2-yl}methyl acetate (145 mg, 0.451 mmol) in ethanol (3.1 mL). The mixture was stirred at 80° C. for 1 h. The reaction was cooled to room temperature and diluted with water (1.0 mL). Lithium hydroxide (32.4 mg, 1.35 mmol) was added, and the mixture was stirred for 2 h. The reaction mixture was 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 (95 mg, 63%). LCMS calculated for C16H20N3O3S (M+H)+: m/z=334.1. Found: 334.0.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in ethanol (0.85 mL)
  3. stirringThe mixture was stirred at 80° C. for 1 h
  4. temperatureThe reaction was cooled to room temperature
  5. stirringthe mixture was stirred for 2 h
  6. custompurified with prep-LCMS (XBridge C18 column
  7. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-dacf00127e7648e5a9329792439b417c
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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