Acetic Acid → HCID 58563758, compound

HRID 336187Notes

Reaction equation

HRID 336187 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[O:20]1[CH2:25][CH2:24][CH:23]([CH:26]=O)[CH2:22][CH2:21]1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+].C([BH3-])#N.[Na+]>CN(C=O)C.ClCCl>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]2[CH2:26][CH:23]2[CH2:24][CH2:25][O:20][CH2:21][CH2:22]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 24436Sodium SulfateHCID 5003444Sodium cyanoborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 70864984HCID 70864984, compound

Product 1

HCID 58563758HCID 58563758, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-Piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl) amide; hydrochloride (110 mg; 0.382 mmol) in DMF (1.5 mL) is added tetrahydro-pyran-4-carbaldehyde (87.2 mg; 0.764 mmol), acetic acid (0.022 mL; 0.382 mmol) and sodium sulfate (5-10 equivalents). The mixture is stirred at room temperature for 30 minutes before adding sodium cyanoborohydride (24 mg; 0.382 mmol). The mixture is stirred at room temperature for 18 hours. The mixture is diluted with dichloromethane and washed with saturated NaHCO3 aqueous solution. The organic layer is dried over Na2SO4, filtered and concentrated in vacuo. Crude product is purified by preparative HPLC. Product fractions are pooled and concentrated in vacuo to afford the title compound, m/z 350 [M+H+].

Workup

  1. stirringThe mixture is stirred at room temperature for 18 hours
  2. washwashed with saturated NaHCO3 aqueous solution
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customCrude product is purified by preparative HPLC
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd14d1c53c29421eae2d62ff9eaf2160
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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