Trifluoroacetic acid → [(2Z)-2-[4-[4-chloro-2-(2-methylpyrazol-3-yl)phenoxy]-3-cyanophenyl]sulfonylimino-1,3-thiazol-3-yl]methyl dihydrogen phosphate

HRID 46275ノート

反応式

HRID 46275 の反応式
[P:1]([O:13][CH2:14][N:15]1[CH:19]=[CH:18][S:17]/[C:16]/1=[N:20]\[S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[C:38]2[N:42]([CH3:43])[N:41]=[CH:40][CH:39]=2)=[C:26]([C:44]#[N:45])[CH:25]=1)(=[O:23])=[O:22])([O:8]C(C)(C)C)([O:3]C(C)(C)C)=[O:2].FC(F)(F)C(O)=O>C(OCC)(=O)C.ClCCl.C(O)C.CO>[P:1]([OH:8])([OH:3])([O:13][CH2:14][N:15]1[CH:19]=[CH:18][S:17]/[C:16]/1=[N:20]\[S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[C:38]2[N:42]([CH3:43])[N:41]=[CH:40][CH:39]=2)=[C:26]([C:44]#[N:45])[CH:25]=1)(=[O:22])=[O:23])=[O:2]

参加物

7

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 59436487ditert-butyl [(2Z)-2-[4-[4-chloro-2-(2-methylpyrazol-3-yl)phenoxy]-3-cyanophenyl]sulfonylimino-1,3-thiazol-3-yl]methyl phosphate

生成物 1

HCID 59436471[(2Z)-2-[4-[4-chloro-2-(2-methylpyrazol-3-yl)phenoxy]-3-cyanophenyl]sulfonylimino-1,3-thiazol-3-yl]methyl dihydrogen phosphate

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Di-tert-butyl [(2Z)-2-[({4-[4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-3-cyanophenyl}sulfonyl)imino]-1,3-thiazol-3(2H)-yl]methyl phosphate, (Example 1040, 250 mg, 0.00036 mol) was dissolved in ethyl acetate (10 mL) and then trifluoroacetic acid (1 mL) was added. The solution was stirred at room temperature for 3 hours, then a further portion of trifluoroacetic acid (2 mL) was added and stirred at room temperature for 18 hours. The solvents were removed in vacuo and the residue was partitioned between tert-butylmethyl ether (30 mL) and water (40 mL) and a few drops of aqueous sodium hydroxide solution (2 molar). The aqueous layer was then acidified to pH 1-2 with aqueous hydrochloric acid (2 molar) to give a sticky cream precipitate which was dissolved in a mixture of dichloromethane, ethanol and methanol. This organic layer was dried over anhydrous sodium sulphate, filtered and the solvents removed in vacuo to give the crude product which was triturated with ethyl acetate to give the title compound as a buff powder, (85 mg).

後処理

  1. stirringstirred at room temperature for 18 hours
  2. customThe solvents were removed in vacuo
  3. customthe residue was partitioned between tert-butylmethyl ether (30 mL) and water (40 mL) and a few drops of aqueous sodium hydroxide solution (2 molar)
  4. customto give a sticky cream precipitate which
  5. dry with materialThis organic layer was dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customthe solvents removed in vacuo
  8. customto give the crude product which
  9. customwas triturated with ethyl acetate

出典と根拠

ORDレコード
ord-b9e73e81fd044053be27216c3a342cbe
出典データセット
uspto-grants-2013_09
特許番号
US08541588B2

反応ノート

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