Triethylamine → N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine

HRID 1506750ノート

反応式

HRID 1506750 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C1COCC1>[CH3:24][S:25]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:16])(=[O:27])=[O:26]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3366758Benzyl N-(4-hydroxybutyl)carbamate

生成物 1

HCID 11141145N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine収率 81.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
22.5 °C

実験手順

To a solution of benzyl 4-hydroxybutylcarbamate (1.1 g, 4.9 mmol) and triethylamine (1.7 mL, 9.8 mmol) in THF was added methanesulfonyl chloride (0.67 g, 5.9 mmol) at 0° C. The reaction was stirred at 20-25° C. for 6 hours and concentrated. The residue was partitioned between ethyl acetate and water. The phases were separated, and the organic layer was washed with hydrochloride solution (1 N), saturated sodium bicarbonate solution, and saline. The separated organic layer was dried and concentrated to give 4-(benzyloxycarbonylamino)butyl methanesulfonate (1.2 g).

後処理

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe phases were separated
  4. washthe organic layer was washed with hydrochloride solution (1 N), saturated sodium bicarbonate solution, and saline
  5. customThe separated organic layer was dried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-b20122d48fe34482a3c16ad8d8803456
出典データセット
uspto-grants-2015_12
特許番号
US09221760B2

反応ノート

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