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

HRID 451303ノート

反応式

HRID 451303 の反応式
[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

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86659587HCID 86659587、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9d7899519cb24cdca09d3c3a8824f350
出典データセット
uspto-grants-2013_07
特許番号
US08487093B2

反応ノート

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