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

HRID 1506750노트

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HRID 1506750 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 11141145N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine수율 81.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
22.5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b20122d48fe34482a3c16ad8d8803456
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221760B2

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