Hydrochloric Acid → ethyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-((S)-1-hydroxymethyl-2-methylpropylamino)acrylate

HRID 1967450

反応式

HRID 1967450 の反応式
[Br:1][C:2]1[C:3]([O:22][CH3:23])=[CH:4][C:5]([O:20][CH3:21])=[C:6]([CH:19]=1)[C:7]([C:9](=[CH:15]N(C)C)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8].[NH2:24][C@H:25]([CH2:29][OH:30])[CH:26]([CH3:28])[CH3:27].Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([O:22][CH3:23])=[CH:4][C:5]([O:20][CH3:21])=[C:6]([CH:19]=1)[C:7]([C:9](=[CH:15][NH:24][C@H:25]([CH2:29][OH:30])[CH:26]([CH3:28])[CH3:27])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 640993L-ValinolHCID 66985486Ethyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-dimethylaminoacrylate

生成物 1

HCID 69031975ethyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-((S)-1-hydroxymethyl-2-methylpropylamino)acrylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Under a nitrogen atmosphere, to a solution of ethyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-dimethylaminoacrylate obtained in Step 4 of Example 1 in toluene was added L-valinol (20.6 g). After stirring at room temperature for 1 hr, the completion of the reaction was confirmed by HPLC. 1 mol/L Hydrochloric acid (200 mL) was added to the reaction mixture, and after stirring, the toluene layer was separated. The toluene layer was further washed successively with 1 mol/L hydrochloric acid (200 mL), water (200 mL), 5% aqueous sodium hydrogencarbonate solution (200 mL) and water (200 mL). After washing, toluene was evaporated under reduced pressure, toluene (200 mL) was added to the concentrated residue, and the mixture was concentrated again under reduced pressure. THF (200 mL) was further added to the concentrated residue, and the mixture was concentrated again under reduced pressure. THF (160 mL) was added to the obtained concentrated residue to give ethyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-((S)-1-hydroxymethyl-2-methylpropylamino)acrylate as a tetrahydrofuran solution. The solution was directly used in the next step.

後処理

  1. stirringafter stirring
  2. customthe toluene layer was separated
  3. washThe toluene layer was further washed successively with 1 mol/L hydrochloric acid (200 mL), water (200 mL), 5% aqueous sodium hydrogencarbonate solution (200 mL) and water (200 mL)
  4. washAfter washing
  5. customtoluene was evaporated under reduced pressure, toluene (200 mL)
  6. additionwas added to the concentrated residue
  7. concentrationthe mixture was concentrated again under reduced pressure
  8. additionTHF (200 mL) was further added to the concentrated residue
  9. concentrationthe mixture was concentrated again under reduced pressure
  10. additionTHF (160 mL) was added to the obtained concentrated residue

出典と根拠

ORDレコード
ord-4030a6694aaf4968936276cd0de5717b
出典データセット
uspto-grants-2013_04
特許番号
US08420821B2

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