Triethylamine → HCID 67274011, compound

HRID 599790Notes

Reaction equation

HRID 599790 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 8028TetrahydrofuranSolvent

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 was added dropwise and after the addition had ended the reaction solution was stirred for 30 min without cooling. 15 mL of 4 N NaOH were added (temperature increase to 20° C.), the mixture was stirred for another 5 min, cooled to 0° C., combined with 50 mL MTBE and stirred for 20 min. The organic phase was separated off and dried on Na2SO4. After the elimination of the desiccant and solvent the residue was reacted further without any purification.

Workup

  1. additionafter the addition
  2. stirringwas stirred for 30 min
  3. temperaturewithout cooling
  4. temperature(temperature increase to 20° C.)
  5. stirringthe mixture was stirred for another 5 min
  6. temperaturecooled to 0° C.
  7. stirringstirred for 20 min
  8. customThe organic phase was separated off
  9. customdried on Na2SO4
  10. customAfter the elimination of the desiccant and solvent the residue was reacted further without any purification

Sources & evidence

ORD record
ord-0a858c7204454943aa7838b79a814549
Source dataset
uspto-grants-2011_03
Patent number
US07897603B2

Reaction notes

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