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Sodium Azide → HCID 57300086、化合物

HRID 1740476
ノート
印刷プレビュー

反応式

HRID 1740476 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][C@@H:9]1[CH2:24][O:25][C:26]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:49]=[N+:50]=[N-:51].[Na+]>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:49]=[N+:50]=[N-:51])[CH2:10][C@@H:9]1[CH2:24][O:25][C:26]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:35]1[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=1)[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 54480540HCID 54480540、化合物

生成物 1

HCID 57300086HCID 57300086、化合物収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

(2R,4R)-1-(tert-Butyloxycarbonyl)-2-(4,4'-Dimethoxytrityl)oxymethyl-4-[(p-toluenesulfonyl)oxy]pyrrolidine 39 (5.1 g, 7.58 mmol) was dissolved in dimethylformamide (50 ml) and diluted with water (5 ml ). To this stirred solution was added sodium azide (0.65 g, 10 mmol) and heated at 80° C. for 8 h. It was cooled and evaporated to dryness. The residue was partitioned between CH2Cl2 (200 ml) and water (100 ml), and extracted in CH2Cl2. The organic extract was washed with brine (50 ml), dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography over silica gel using hexane→EtOAc as the eluent. The pure fractions were pooled together and evaporated to give 3.8 g (92%) of a clear oil. 1HNMR (CDCl3): 1.45 (s, 9H, Boc), 1.90 (dd, 1H), 2.34 (m, 1H), 3.40-3.62 (m, 3H), 3.74 (s, 6H, 2.0CH3), 4.00 (m, 2H), 4.28 (bs, 1H), 4.44 (m, 1H), 6.82 (d, 4H, Ph), and 7.26-7.80 (m, 9H, Ph).

後処理

  1. temperatureIt was cooled
  2. customevaporated to dryness
  3. customThe residue was partitioned between CH2Cl2 (200 ml) and water (100 ml)
  4. extractionextracted in CH2Cl2
  5. extractionThe organic extract
  6. washwas washed with brine (50 ml)
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness
  9. customThe crude product was purified by flash chromatography over silica gel
  10. customevaporated

出典と根拠

ORDレコード
ord-18ca873b27a74843aa87c2882610be59
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05969135

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート