Triethylamine → HCID 67301704, compound

HRID 643614Notes

Reaction equation

HRID 643614 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[CH3:15].[CH2:16](N(CC)CC)C>C1COCC1>[NH2:1][C:2]1[C:3]([CH3:15])=[CH:4][C:5]([CH2:9][C@@H:10]([OH:14])[C:11]([O:13][CH3:16])=[O:12])=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 67301639HCID 67301639, compound

Product 1

HCID 67301704HCID 67301704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-35 °C

Procedure

Under a nitrogen atmosphere a mixture of 20.0 g (82.1 mmol) 3-(4-amino-3,5-dimethyl-phenyl)-2-oxo-propionic acid and 25.7 mL (189 mmol) triethylamine in 400 mL THF was cooled to −35° C. Then a solution of 40.0 g (125 mmol) (1R)—B-chlorodiisopinocampheylborane in 100 mL THF was added dropwise so that the reaction temperature remained between −35° C. and −25° C. The reaction mixture was kept for 1 h at this temperature, the cooling bath was removed and the reaction mixture was stirred overnight at RT. THF was evaporated down i.vac., the residue was combined with methanolic HCl (1.25 M) and stirred for 2 h at RT. It was evaporated down i.vac., the residue was taken up in 2 M HCl and extracted exhaustively with EtOAc. The aqueous phase was made alkaline with semiconc. NaOH and exhaustively extracted with EtOAc. The combined organic phases were dried over Na2SO4, suction filtered through activated charcoal and evaporated down. The product was obtained as a brown oil.

Workup

  1. customremained between −35° C. and −25° C
  2. customthe cooling bath was removed
  3. customTHF was evaporated down i.vac
  4. stirringstirred for 2 h at RT
  5. customIt was evaporated down i.vac
  6. extractionextracted exhaustively with EtOAc
  7. extractionNaOH and exhaustively extracted with EtOAc
  8. dry with materialThe combined organic phases were dried over Na2SO4, suction
  9. filtrationfiltered through activated charcoal
  10. customevaporated down
  11. customThe product was obtained as a brown oil

Sources & evidence

ORD record
ord-917acd8412124e03b7605b025f8710a8
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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