Triethylamine → HCID 69493341, compound

HRID 642813Notes

Reaction equation

HRID 642813 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12](=[O:16])[C:13]([OH:15])=[O:14])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[CH2:17](N(CC)CC)[CH3:18]>C1COCC1>[OH:16][C@H:12]([CH2:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([CH3:1])[CH:3]=1)[NH:9][N:8]=[CH:7]2)[C:13]([O:15][CH2:17][CH3:18])=[O:14]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 68609409HCID 68609409, compound

Product 1

HCID 69493341HCID 69493341, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

A solution of 2.31 g (7.2 mmol) (1R)—B-chlorodiisopinocampheylborane in 20 mL THF was added dropwise within 30 min to a solution of 1.3 g (5.96 mmol) 3-(7-methyl-1H-indazol-5-yl)-2-oxo-propionic acid and 0.84 mL (7.2 mmol) triethylamine in 50 mL THF cooled to approx. −25° C. and the reaction mixture was kept for 1.5 h at this temperature and then heated to RT within another hour. The mixture was evaporated down i.vac., the residue was taken up in 100 mL 4 M ethanolic HCl and stirred overnight at RT. 200 mL EtOAc and 200 mL 15% K2CO3 solution were added, the organic phase was separated off and dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was purified chromatographically by HPLC.

Workup

  1. temperatureheated to RT within another hour
  2. customThe mixture was evaporated down i.vac
  3. addition200 mL EtOAc and 200 mL 15% K2CO3 solution were added
  4. customthe organic phase was separated off
  5. dry with materialdried over Na2SO4
  6. customwas purified chromatographically by HPLC

Sources & evidence

ORD record
ord-d8d8327e14254297a2475da5e2540911
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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