Triethylamine → HCID 178454136, 화합물

HRID 707266노트

반응식

HRID 707266 반응식
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@H:10]([OH:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:12][C@H:10]1[CH2:11][C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:13])[CH2:9]1)(=[O:24])=[O:23]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178454126HCID 178454126, 화합물

생성물 1

HCID 178454136HCID 178454136, 화합물수율 102%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl(trans-3-hydroxycyclobutyl)carbamate (20.05 g, 107 mmol) and triethylamine, anhydrous (22.34 mL, 161 mmol) in DCM (200 mL) was cooled to −30° C. and methanesulfonyl chloride (9.94 mL, 129 mmol) was added dropwise over 20 min period. The mixture was stirred at room temperature for 12 h, washed with 200 mL water, then 200 mL 10% aq. citric acid followed by brine, dried over Na2SO4 and evaporated to give the desired product trans-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (29 g, 109 mmol, 102% yield), which was used in the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.03-5.25 (m, 1 H), 4.73 (br. s., 1 H), 4.27 (br. s., 1 H), 3.00 (s, 3 H), 2.67 (ddd, J=13.60, 8.51, 4.50 Hz, 2 H), 2.44 (dt, J=12.86, 6.19 Hz, 2 H), 1.33-1.53 (m, 9 H).

후처리

  1. washwashed with 200 mL water
  2. dry with materialdried over Na2SO4
  3. customevaporated

출처 및 근거

ORD 기록
ord-6f4abf16bfd54eb8b94b83af3ec8c673
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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