Sodium hydride → HCID 131735581、化合物

HRID 524362ノート

反応式

HRID 524362 の反応式
[H-].[Na+].[Si:3]([O:20][CH2:21][C@H:22]1[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[NH:23]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:30][CH2:31][CH2:32][C:33]1[S:37][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:34]=1>CN(C=O)C>[Si:3]([O:20][CH2:21][C@H:22]1[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[N:23]1[CH2:30][CH2:31][CH2:32][C:33]1[S:37][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:34]=1)([C:16]([CH3:17])([CH3:18])[CH3:19])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 67300712HCID 67300712、化合物HCID 131735580(R)-3-(((tert-Butyldiphenylsilyl)oxy)methyl)isothiazolidine 1,1-dioxide

生成物 1

HCID 131735581HCID 131735581、化合物収率 92.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To a mixture of sodium hydride (37 mg, 1.54 mmol) in DMF (3.0 mL) cooled to 0° C. was added dioxide 8 (554 mg, 1.42 mmol). After 0.5 h a solution methyl 5-(3-iodopropyl)thiophene-2-carboxylate (485 mg, 1.56 mmol) in DMF (4.5 mL). The reaction was allowed to warm to room temperature on its own accord and stirred for 16 h. The reaction was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex) afforded 751 mg (91%) of ester 9.

後処理

  1. temperatureto warm to room temperature on its own accord
  2. customThe reaction was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with EtOAc
  4. washThe organic portion was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex)

出典と根拠

ORDレコード
ord-5615229e6e034aa0ba265a1ceaead14b
出典データセット
uspto-grants-2016_05
特許番号
US09340534B2

反応ノート

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