Ethyl Acetate → (R)-3-t-butyloxycarbonylamino-1-carbomethoxymethyl-3,4-dihydrocarbostyril

HRID 31119

反応式

HRID 31119 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].C[O-].[Na+].C(OCC)(=O)C>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:10]1=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 60984Methyl bromoacetateHCID 10942334Sodium MethoxideHCID 69198597(R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril

生成物 1

HCID 69194872(R)-3-t-butyloxycarbonylamino-1-carbomethoxymethyl-3,4-dihydrocarbostyril収率 72.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

(R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (26 mg), as prepared in Example 5, was dissolved in tetrahydrofuran (5 mL) at room temperature under argon. To the stirring solution was added methyl bromoacetate (31 mg), followed by sodium methoxide (26 mg). The resulting suspension was stirred for 30 min before dilution with ethyl acetate (25 mL) and water (25 mL). The organic phase was separated, washed with water (25 mL), and dried over anhydrous sodium sulfate. After solvent evaporation under vacuum, the crude product was purified by reverse phase preparative HPLC to provide (R)-3-t-butyloxycarbonylamino-1-carbomethoxymethyl-3,4-dihydrocarbostyril (24 mg).

後処理

  1. customThe organic phase was separated
  2. washwashed with water (25 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter solvent evaporation under vacuum
  5. customthe crude product was purified by reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-6b3c0673d7ab4fdfaffb6c0713349ba3
出典データセット
uspto-grants-2008_09
特許番号
US07425550B2

関連ノート

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