Chloroacetyl chloride → methyl (5R)-1-(chloroacetyl)-5-((trimethylsilyl)ethynyl)-L-prolinate

HRID 855821

反応式

HRID 855821 の反応式
[CH3:1][Si:2]([C:5]#[C:6][C@@H:7]1[NH:11][C@H:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8]1)([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>O1CCCC1>[Cl:23][CH2:24][C:25]([N:11]1[C@@H:7]([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])[CH2:8][CH2:9][C@H:10]1[C:12]([O:14][CH3:15])=[O:13])=[O:26]

参加物

5

反応物 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 16090847methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

生成物 1

HCID 59683665methyl (5R)-1-(chloroacetyl)-5-((trimethylsilyl)ethynyl)-L-prolinate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of methyl(5R)-5-((trimethylsilyl)ethynyl)-L-prolinate (2.76 g, 12.2 mmol) and triethylamine (2.13 mL, 15.3 mmol) in dry tetrahydrofuran (50 mL) at 0° C. was gradually added a solution of chloroacetyl chloride (0.97 mL, 12.2 mmol) in dry tetrahydrofuran (10 mL). After stirring at room temperature for 2 hours, the mixture was filtered. The solid cake was washed with THF, and the filtrate and washings were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue taken up in toluene and concentrated to dryness under reduced pressure to provide the titled compound. MS (CI) m/z 302 (M+1)+.

後処理

  1. filtrationthe mixture was filtered
  2. washThe solid cake was washed with THF
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-bd1948c6211045bba22a839a3eb3f4c5
出典データセット
uspto-grants-2007_08
特許番号
US07262207B2

関連ノート

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