Trifluoroacetic acid → (2S,5R)-N-[(4S)-Azepan-4-yl]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

HRID 451303노트

반응식

HRID 451303 반응식
[NH:1]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9]([C@@H:11]2[CH2:17][CH2:16][C@@H:15]3[CH2:18][N:12]2[C:13](=[O:24])[N:14]3[O:19][S:20]([O-:23])(=[O:22])=[O:21])=[O:10])[CH2:3][CH2:2]1.C([N+](CCCC)(CCCC)CCCC)CCC.FC(F)(F)C(O)=O>ClCCl>[NH:1]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9]([C@@H:11]2[CH2:17][CH2:16][C@@H:15]3[CH2:18][N:12]2[C:13](=[O:24])[N:14]3[O:19][S:20]([OH:23])(=[O:21])=[O:22])=[O:10])[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86659587HCID 86659587, 화합물

생성물 1

HCID 44183767(2S,5R)-N-[(4S)-Azepan-4-yl]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N,N,N-tributylbutan-1-aminium {[((2S,5R)-2-{[(4S)-azepan-4-ylamino]carbonyl}-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl)oxy]sulfonyl}oxidanide (30.9 mg, 0.067 mmol) in anhydrous dichloromethane (7 mL) at 0° C. under nitrogen was added trifluoroacetic acid (0.5 mL, 6.5 mmol) dropwise. The reaction mixture was stirred for two hours then concentrated under vacuum. Ether was added to the residue and the resulting white precipitate was collected by centrifugation. The precipitate was purified by HPLC on a Phenomenex Synergy Polar-RP 80A column and lyophilized to afford the title compound as a white solid. LC-MS (negative ionization) m/e 361 (M−H); LC-MS (positive ionization) m/e 385 (M+Na); 1H NMR (600 MHz, D2O; unreferenced) (δ, ppm) 4.17 (1H, br d, J=3 Hz), 3.96-4.03 (2H, m), 3.27-3.38 (3H, m), 3.15-3.22 (2H, m), 3.02 (1H, d, J=12 Hz), 1.62-2.18 (m, 12H).

후처리

  1. concentrationthen concentrated under vacuum
  2. additionEther was added to the residue
  3. customthe resulting white precipitate was collected by centrifugation
  4. customThe precipitate was purified by HPLC on a Phenomenex Synergy Polar-RP 80A column

출처 및 근거

ORD 기록
ord-9d7899519cb24cdca09d3c3a8824f350
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487093B2

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