Acetic Acid → HCID 46873307, compound

HRID 336188Notes

Reaction equation

HRID 336188 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(O)(=O)C.C(O[C:27]1(O[Si](C)(C)C)[CH2:29][CH2:28]1)C.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[C:1]([C:5]1[S:9][C:8]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]2[CH:27]2[CH2:29][CH2:28]2)=[O:12])=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 70864983HCID 70864983, compound

Product 1

HCID 46873307HCID 46873307, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-Piperidine-2-carboxylic acid (5-tert-butyl-1,3,4-thiadiazol-2-yl)-amide; hydrochloride (125 mg; 0.41 mmol) in methanol (3 mL) is added acetic acid (0.235 mL; 4.1 mmol), [(1-ethoxycyclopropyl)oxy]trimethylsilane (0.48 mL; 2.4 mmol) and sodium cyanoborohydride (116.25 mg; 1.85 mmol). The reaction mixture is heated at reflux for 5 hours. After cooling, the mixture is diluted with ethyl acetate and washed with saturated NaHCO3 aqueous solution then brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by preparative HPLC affords the title compound, m/z 309 [M+H+].

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 5 hours
  3. temperatureAfter cooling
  4. washwashed with saturated NaHCO3 aqueous solution
  5. dry with materialbrine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-3755cbb7e37344e6a86d8fe069585717
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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