Tetramethyltin → N-Isoamyl-N-(6-methyl naphthalene-2-sulfonyl)-D-valine tert-butyl ester

HRID 77323

反応式

HRID 77323 の反応式
[C:1]([O:5][C:6](=[O:38])[C@@H:7]([CH:35]([CH3:37])[CH3:36])[N:8]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17](OS(C(F)(F)F)(=O)=O)[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].[CH3:41][Sn](C)(C)C>CN(C)C=O.C1(P([Pd](Cl)(Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:38])[C@@H:7]([CH:35]([CH3:36])[CH3:37])[N:8]([CH2:30][CH2:31][CH:32]([CH3:33])[CH3:34])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:41])[CH:18]=2)[CH:13]=1)(=[O:10])=[O:11])([CH3:3])([CH3:4])[CH3:2]

参加物

6

反応物 3

HCID 11661TetramethyltinHCID 433294Lithium ChlorideHCID 86653275N-isoamyl-N-(6-trifluoromethanesulfonyloxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

生成物 1

HCID 67155284N-Isoamyl-N-(6-methyl naphthalene-2-sulfonyl)-D-valine tert-butyl ester収率 50%

試薬・触媒・溶媒 2

HCID 178479802HCID 178479802、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of N-isoamyl-N-(6-trifluoromethanesulfonyloxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (1.1 g, 1.89 mmol) in N,N-dimethylformamide (20 mL) is added lithium chloride (0.40 g, 9.5 mmol), tetramethyl tin (0.525 mL, 3.79 mmol), and bistriphenylphosphino palladium dichloride (0.066 g, 0.095 mmol). The reaction is heated to 80° C. for 16 h. The reaction is allowed to cool to ambient temperature and filtered through Celite. The filtrate is poured over water and extracted three times with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by column chromatography (4% hexanes-ethyl acetate) to afford the title compound as a white solid (0.41 g, 50% yield).

後処理

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered through Celite
  3. additionThe filtrate is poured over water
  4. extractionextracted three times with dichloromethane
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography (4% hexanes-ethyl acetate)

出典と根拠

ORDレコード
ord-457daebb59124a8c80dea501b501c76d
出典データセット
uspto-grants-2014_09
特許番号
US08841291B2

関連ノート

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