Lithium Bromide → Methyl (S)-2-benzyloxycarbonylamino-4-oxo-5-phenylpentanoate

HRID 1367120ノート

反応式

HRID 1367120 の反応式
[Br-].[Li+].[CH2:3]([Mg]Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:12]([O:19][C:20]([NH:22][C@@H:23]([CH2:28][C:29](Cl)=[O:30])[C:24]([O:26][CH3:27])=[O:25])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([O:19][C:20]([NH:22][C@@H:23]([CH2:28][C:29](=[O:30])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:24]([O:26][CH3:27])=[O:25])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 82050Lithium BromideHCID 11055664Methyl (S)-2-benzyloxycarbonylamino-3-chlorocarbonylpropionateHCID 178418336HCID 178418336、化合物

生成物 1

HCID 57535346Methyl (S)-2-benzyloxycarbonylamino-4-oxo-5-phenylpentanoate収率 53.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a suspension of copper(I) bromide-dimethyl sulfide complex (2.6 g, 12.72 mmol, 1.2 eq.) in dry THF was added a solution of lithium bromide (2.2 g, 25.44 mmol, 2.4 eq.) in dry THF. The mixture was stirred at room temperature (RT) for 20 min, and then was cooled to −78° C. A solution of benzyl magnesium chloride (13 mL, 12.72 mmol, 1.2 eq.) followed by a solution of (S)-methyl 2-(benzyloxycarbonylamino)-4-chloro-4-oxobutanoate (3.16 g, 10.6 mmol, 1 eq.) in dry THF were added. The mixture was stirred at −78° C. for 30 min and then was quenched with sat. ammonium chloride. The mixture was extracted with ethyl acetate. The organic layers were dried over magnesium sulfate and then concentrated in vacuo. The residue was purified by flash column (1:1 ethyl acetate:hexane) to give 2 g of (S)-methyl 2-(benzyloxycarbonylamino)-4-oxo-5-phenylpentanoate.

後処理

  1. temperaturewas cooled to −78° C
  2. additionwere added
  3. stirringThe mixture was stirred at −78° C. for 30 min
  4. customwas quenched with sat. ammonium chloride
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layers were dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column (1:1 ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-aef32272730243739c7099d05b8a1950
出典データセット
uspto-grants-2011_02
特許番号
US07893112B2

反応ノート

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