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Benzyl Bromide → 3(R)-Benzyl-5(S)-[5-benzyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxotetrahydrofuran

HRID 863271
ノート
印刷プレビュー

反応式

HRID 863271 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH3:29])([CH3:28])[CH2:12][C@@H:13]([C@H:22]1[O:26][C:25](=[O:27])[CH2:24][CH2:23]1)[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1>[CH2:40]([C@@H:24]1[CH2:23][C@@H:22]([C@@H:13]([NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:12][C:11]([CH3:29])([CH3:28])[CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:26][C:25]1=[O:27])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 2733832Lithium hexamethyldisilazaneHCID 867521045(S)-[5-Benzyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxotetrahydrofuran

生成物 1

HCID 676254563(R)-Benzyl-5(S)-[5-benzyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxotetrahydrofuran

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒
4 回

実験手順

A solution of 1.76 g of 5(S)-[5-benzyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethylpentyl]-2-oxo-tetrahydrofuran in 30 ml of tetrahydrofuran is added to a mixture of 9.14 ml of a 1M lithiumbis(trimethylsilyl)amide solution in tetrahydrofuran and 30 ml of tetrahydrofuran at -78° C. under argon and the mixture is stirred for 30 min. 0.63 ml of benzyl bromide in 30 ml of tetrahydrofuran are then added dropwise. After the mixture has been stirred at -78° C. for 3.5 h, the reaction is quenched by addition of 1.6 ml of propionic acid and the mixture is diluted with diethyl ether. The organic phase is washed with a 10% aqueous citric acid solution and a 1M sodium bicarbonate solution, dried over sodium sulfate and concentrated. Purification over silica gel (mobile phase D) gives the title compound: Rf (D)=0.23; FAB-MS: (M+H)+ =496.

後処理

  1. stirringAfter the mixture has been stirred at -78° C. for 3.5 h
  2. customthe reaction is quenched by addition of 1.6 ml of propionic acid
  3. additionthe mixture is diluted with diethyl ether
  4. washThe organic phase is washed with a 10% aqueous citric acid solution
  5. dry with materiala 1M sodium bicarbonate solution, dried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification over silica gel (mobile phase D)

出典と根拠

ORDレコード
ord-71cb43efcd514b0a8aa336b0c4968d9d
出典データセット
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05719141

反応ノート

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