Trifluoroacetic acid → Dimethyl {[({[4-({[2-amino-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]amino}carbonyl) oxy]methyl}phosphonate

HRID 1013535ノート

反応式

HRID 1013535 の反応式
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:40]=[CH:39][C:26]([CH2:27][NH:28][C:29]([O:31][CH2:32][P:33](=[O:38])([O:36][CH3:37])[O:34][CH3:35])=[O:30])=[CH:25][CH:24]=1)=[O:22])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:24]=[CH:25][C:26]([CH2:27][NH:28][C:29]([O:31][CH2:32][P:33](=[O:38])([O:36][CH3:37])[O:34][CH3:35])=[O:30])=[CH:39][CH:40]=1)=[O:22]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 57925842Dimethyl {[({[4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]amino}carbonyl)oxy]methyl}phosphonate

生成物 1

HCID 57925826Dimethyl {[({[4-({[2-amino-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]amino}carbonyl) oxy]methyl}phosphonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Dimethyl {[({[4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]amino}carbonyl)oxy]methyl}phosphonate 0.496 g, 0.841 mmol) was dissolved in DCM (4 ml). TFA (1 ml, 12.98 mmol) was added. The reaction was allowed to stir for ˜1 h 15 min. The reaction was diluted with DCM and washed with saturated aqueous sodium hydrogen carbonate. The aqueous layer was extracted three times with DCM. The combined organic layers were dried over Na2SO4, filtered, and concentrated. 1H NMR (DMSO-d6, 600 MHz) δ 9.67 (s, 1H), 8.13 (t, J=6.3 Hz, 1H), 7.93 (d, J=7.9 Hz, 2H), 7.44 (bs, 1H), 7.35 (d, J=7.9 Hz, 2H), 7.32 (dd, J=5.1 Hz, 1.0 Hz, 1H), 7.26 (dd, J=8.4 Hz, 2.2 Hz, 1H), 7.21 (d, J=3.1 Hz, 1H), 7.01 (dd, J=5.1 Hz, 3.7 Hz, 1 H), 6.77 (d, J=8.2 Hz, 1H), 5.11 (s, 2H), 4.39 (d, J=7.9 Hz, 2H), 4.25 (d, J=6.2 Hz, 2H), 3.66 (d, J=10.6 Hz, 6H). MS: calc'd 490 (MH+), exp 490 (MH+).

後処理

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. extractionThe aqueous layer was extracted three times with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-11340297368c4fd4b2688596283bb51f
出典データセット
uspto-grants-2011_07
特許番号
US07981874B2

反応ノート

読み込み中…