Triethylamine → HCID 67274011, compound

HRID 643119Notes

Reaction equation

HRID 643119 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C:17](=[O:21])[C:18]([OH:20])=[O:19])=[CH:11][C:10]=1[CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[OH-].[Na+].CC(OC)(C)C>C1COCC1>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C@@H:17]([OH:21])[C:18]([OH:20])=[O:19])=[CH:11][C:10]=1[CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 67273229HCID 67273229, compound

Product 1

HCID 67274011HCID 67274011, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

Under an argon atmosphere a solution of 9.59 g (30.7 mmol) 3-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-2-oxo-propionic acid in 25 mL THF was combined with 4.26 mL (31.0 mmol) triethylamine, stirred for 5 min and cooled to −30° C. (internal temperature). A solution of 19.7 g (61.0 mmol) (1R)-B-chlorodiisopinocampheylborane in 35 mL THF was added dropwise and after the end of the addition the reaction solution was stirred for 30 min without cooling. 15 mL 4 N NaOH was added (temperature rose to 20° C.), the mixture was stirred for 5 min, cooled to 0° C., combined with 50 mL MTBE and stirred for 20 min. The organic phase was separated off and dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was further reacted without purification.

Workup

  1. additionafter the end of the addition the reaction solution
  2. stirringwas stirred for 30 min
  3. temperaturewithout cooling
  4. stirringthe mixture was stirred for 5 min
  5. temperaturecooled to 0° C.
  6. stirringstirred for 20 min
  7. customThe organic phase was separated off
  8. dry with materialdried over Na2SO4
  9. customwas further reacted without purification

Sources & evidence

ORD record
ord-a031c7f7ac274dad94c6d8f4c7bc56ca
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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