Imidazole → 2-(Tertbutyldiphenylsilyloxy)propanamide

HRID 872857

反応式

HRID 872857 の反応式
[OH:1][CH:2]([CH3:6])[C:3]([NH2:5])=[O:4].[C:7]([Si:11](Cl)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:10])([CH3:9])[CH3:8].N1C=CN=C1>CN(C)C1C=CN=CC=1.CN(C=O)C>[Si:11]([O:1][CH:2]([CH3:6])[C:3]([NH2:5])=[O:4])([C:7]([CH3:10])([CH3:9])[CH3:8])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 94220Lactamide

生成物 1

HCID 671685282-(Tertbutyldiphenylsilyloxy)propanamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
90 °C

実験手順

2-hydroxy-propanamide (227 mg, 2.55 mmol), DMF (2 ml), tert-butylchlorodiphenyl-silane (1.0 ml, 1057 mg), imidazole (266 mg, 3.91 mmol) and 4-dimethylaminopyridine (93 mg, 0.764 mmol) dissolved in DMF (2 ml) were stirred under nitrogen atmosphere over the weekend. After the weedend the temperature was raised to 90° C. and was left to react for another 4 h. The mixture was then evaporated and extracted with DCM/water and the combined organic phases were evaporated. The product was purified by column chromatography. 1H-NMR (400 MHz; DMSO-d6): δ 1.04 (d, 9H), 1.12 (d, 3H), 4.00 (q, 1H), 7.04 (bs, 1H), 7.24 (bs, 1H), 7.40-7.51 (m, 6H), 7.58-7.66 (m, 4H).

後処理

  1. waitwas left
  2. customto react for another 4 h
  3. customThe mixture was then evaporated
  4. extractionextracted with DCM/water
  5. customthe combined organic phases were evaporated
  6. customThe product was purified by column chromatography

出典と根拠

ORDレコード
ord-eb2b3a4fee3041a6a03a36b281c8db46
出典データセット
uspto-grants-2015_03
特許番号
US08975254B2

関連ノート

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