Citric Acid → HCID 90411475、化合物

HRID 1754597ノート

反応式

HRID 1754597 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([O:19][CH2:20][C@H:21]([C@H:24]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH3:25])[CH2:22][OH:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:23][CH2:22][C@@H:21]([CH2:20][O:19][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@H:24]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH3:25])(=[O:9])=[O:8])=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 11067317(2R,3R)-2-((benzyloxy)methyl)-3-(tert-butyldimethylsiloxy)butan-1-ol

生成物 1

HCID 90411475HCID 90411475、化合物

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

実験手順

p-Toluenesulfonyl chloride (1.4 g. 7.4 mmol) was added in one portion to a cold (ice/water bath) stirred solution of 4 (2.0 g, 6.16 mmol) in anhydrous pyridine (25 ml). The reaction was allowed to warm up to room temperature and stirred for 6 hrs until no starting material was found by HPLC analysis. Ethyl acetate (100 ml) and 10% citric acid (enough to neutralize pyridine) were added. The organic phase was washed with saturated NaCl, saturated NaHCO3 and dried over MgSO4. The crude tosylate 9 (2.9 g) was used in the next step without additional purification. 1H NMR (CDCl3): δ 7.80 (d, J=8.1 Hz, 2H). 7.40-7.25 (m, 7H), 4.41 (d, J=3.6 Hz, 2H), 4.25 (m, 1H), 4.11 (m, 1H), 3.98 (m, 1H), 3.45 (m, 2H), 2.45 (s, 3H), 1.96 (m, 1H), 1.12 (d, J=6.3 Hz, 3H), 0.83 (s, 9H), 0.036 (s, 3H), 0.00 (s, 3H).

後処理

  1. additionwere added
  2. washThe organic phase was washed with saturated NaCl, saturated NaHCO3
  3. dry with materialdried over MgSO4
  4. customThe crude tosylate 9 (2.9 g) was used in the next step without additional purification

出典と根拠

ORDレコード
ord-09dc76da97d5471bab790ce85632f0de
出典データセット
uspto-grants-2015_10
特許番号
US09169256B2

反応ノート

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