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

HRID 1013535노트

반응식

HRID 1013535 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-11340297368c4fd4b2688596283bb51f
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981874B2

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