Triethylamine → HCID 86632302, compound

HRID 643599Notes

Reaction equation

HRID 643599 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH2:13][C:14](=[O:18])[C:15]([OH:17])=[O:16])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.[OH-].[Na+].CC(OC)(C)C>C1COCC1>[F:1][C:2]([F:19])([F:20])[C:3]1[CH:4]=[C:5]([CH2:13][C@@H:14]([OH:18])[C:15]([OH:17])=[O:16])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 57266273HCID 57266273, compound

Product 1

HCID 86632302HCID 86632302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

16.1 g (53.6 mmol) 3-(3,5-bis-trifluoromethyl-phenyl)-2-oxo-propionic acid in 9.5 (70.0 mmol) triethylamine and 100 mL THF were combined at −35° C. with a solution of 26.0 (81.1 mmol) (1R)—B-chlorodiisopinocampheylborane in 40 mL THF within 30 min, stirred for 1 h at this temperature and stirred overnight at RT. After the reaction had ended the reaction mixture was made alkaline at 0° C. with 160 mL 1 M NaOH, stirred for 15 min, combined with 100 mL TBME and the phases were separated. The organic phase was washed with 50 mL water and 50 mL 1 M NaOH. The combined aqueous phases were acidified with 4 M HCl, exhaustively extracted with TBME, the combined organic phases were dried over Na2SO4, suction filtered through activated charcoal and evaporated down i.vac. The product was reacted further without purification.

Workup

  1. stirringstirred overnight at RT
  2. customat 0° C.
  3. stirringstirred for 15 min
  4. customthe phases were separated
  5. washThe organic phase was washed with 50 mL water and 50 mL 1 M NaOH
  6. extractionexhaustively extracted with TBME
  7. dry with materialthe combined organic phases were dried over Na2SO4, suction
  8. filtrationfiltered through activated charcoal
  9. customevaporated down i.vac
  10. customThe product was reacted further without purification

Sources & evidence

ORD record
ord-02ba45f921ad43eb915abb90c2aca889
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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