1,4-Diiodobutane → HCID 58331116、化合物

HRID 625826ノート

反応式

HRID 625826 の反応式
[C:1]([NH:8][C@H:9]([C:16]([O:18][CH3:19])=[O:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[I:30][CH2:31][CH2:32][CH2:33][CH2:34]I>O1CCCC1>[C:4]([O:3][C:1]([NH:8][C@@H:9]([CH2:10][C@H:11]([CH2:34][CH2:33][CH2:32][CH2:31][I:30])[C:12]([O:14][CH3:15])=[O:13])[C:16]([O:18][CH3:19])=[O:17])=[O:2])([CH3:7])([CH3:6])[CH3:5]

参加物

5

反応物 3

HCID 123371,4-DiiodobutaneHCID 2733832Lithium HexamethyldisilazideHCID 2734644Dimethyl N-(tert-Butoxycarbonyl)-L-glutamate

生成物 1

HCID 58331116HCID 58331116、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

5.51 g (20 mmol) of dimethyl Boc-glutamate were dissolved in 60 ml of tetrahydrofuran and cooled to −70° C. Over a period of one hour, 44 ml (44 mmol) of a 1M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran were added dropwise at this temperature, and the mixture was stirred at −70° C. for 2 hours. 18.60 g (60 mmol) of 1,4-diiodobutane were then added dropwise, and after 2 h at this temperature the cooling bath is removed and 100 ml of 2N hydrochloric acid and 300 ml of ethyl acetate were added. The organic phase was separated off, washed with water until neutral, dried over sodium sulphate and filtered, and the filtrate was concentrated. The crude product obtained in this manner was chromatographed on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

後処理

  1. customafter 2 h at this temperature the cooling bath is removed
  2. addition100 ml of 2N hydrochloric acid and 300 ml of ethyl acetate were added
  3. customThe organic phase was separated off
  4. washwashed with water until neutral,
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-06de5d5d47034f729dc10913f8ae03c3
出典データセット
uspto-grants-2016_04
特許番号
US09308282B2

反応ノート

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