Acetic Acid → HCID 46872867, compound

HRID 336189Notes

Reaction equation

HRID 336189 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[S:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(O)(=O)C.[CH2:24]1[CH:29]([CH:30]=O)[CH2:28][CH2:27][O:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]2[CH2:30][CH:29]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:12])[S:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 70865120HCID 70865120, compound

Product 1

HCID 46872867HCID 46872867, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of (S)-Piperidine-2-carboxylic acid (3-tert-butyl-isothiazol-5-yl)-amide; hydrochloride (40.4 mg; 0.11 mmol) in DMF (1 mL) is added acetic acid (0.05 mL; 0.87 mmol) and a solution of tetrahydropyranyl-4-carboxaldehyde (37.7 mg; 0.33 mmol) in DMF (1 mL). The reaction is shaken for 4 hours. To the mixture is added a solution of sodium triacetoxyborohydride (93.2 mg; 0.44 mmol) in DMF (0.4 mL). The reaction mixture is shaken for 16 hours at room temperature. After this time, the reaction is quenched with water (0.1 mL) and the mixture is concentrated in vacuo. Purification by preparative HPLC provides the title compound, m/z 366 [M+H+].

Workup

  1. stirringThe reaction mixture is shaken for 16 hours at room temperature
  2. customAfter this time, the reaction is quenched with water (0.1 mL)
  3. concentrationthe mixture is concentrated in vacuo
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-46dd153525a941a9a04acf87e761766b
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

Loading…