Lithium Hydroxide → HCID 66553817, compound

HRID 397599Notes

Reaction equation

HRID 397599 reaction equation
Cl.[CH3:2][NH:3][C@H:4]([C:22]([OH:24])=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[O:20][CH3:21])=[CH:8][CH:7]=1.[Li+].[OH-:26].CO.[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>O>[CH:17]1[C:30]2[CH:29]([CH2:33][O:32][C:2]([NH:3][C@H:4]([C:22]([OH:24])=[O:23])[CH2:5][C:6]3[CH:7]=[CH:8][C:9]([C:12]4[C:13]([O:20][CH3:21])=[CH:14][CH:15]=[CH:16][C:17]=4[O:18][CH3:19])=[CH:10][CH:11]=3)=[O:26])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:31]=2[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 69969636HCID 69969636, compound

Product 1

HCID 66553817HCID 66553817, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-(2,6-dimethoxyphenyl)-L-phenylalanine hydrochloride (3.53 g, 10 mmol) obtained in step 3 in Example 50 was dissolved in methanol/THF. A solution of LiOH (927 mg) in water (10 ml) was added to the obtained solution. After stirring for 40 minutes, the reaction solution was filtered, and the filtrate was concentrated under reduced pressure and then subjected to the azeotropic distillation with ethanol twice. The obtained solid was dissolved in acetone/water (20 ml/20 ml). Sodium hydrogencarbonate (1.68 g) and Fmoc-Osu (3.37 g) were added to the obtained solution, and they were stirred for 19 hours. The reaction solution was adjusted to pH 2 with concentrated hydrochloric acid. After the extraction with a solvent mixture of isopropanol/dichloromethane (1/1), the extract was concentrated under reduced pressure. The product was purified by the silica gel column chromatography (hexane, hexane/ethyl acetate, 2/1, 3/2) to obtain 5.74 g (100%) of the intended compound.

Workup

  1. filtrationthe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. distillationsubjected to the azeotropic distillation with ethanol twice
  4. dissolutionThe obtained solid was dissolved in acetone/water (20 ml/20 ml)
  5. additionSodium hydrogencarbonate (1.68 g) and Fmoc-Osu (3.37 g) were added to the obtained solution, and they
  6. stirringwere stirred for 19 hours
  7. extractionAfter the extraction
  8. additionwith a solvent mixture of isopropanol/dichloromethane (1/1)
  9. concentrationthe extract was concentrated under reduced pressure
  10. customThe product was purified by the silica gel column chromatography (hexane, hexane/ethyl acetate, 2/1, 3/2)

Sources & evidence

ORD record
ord-156b5599ec16455a84b389a1bf3ec3f5
Source dataset
uspto-grants-2003_08
Patent number
US06610710B2

Reaction notes

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