Trifluoroacetic anhydride → HCID 68864572、化合物

HRID 1726000ノート

反応式

HRID 1726000 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:13]([C:25]([O:27][CH3:28])=[O:26])=[C:14]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)[CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:9].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[O-]S(C(F)(F)F)(=O)=O.[Ga+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>ClC(Cl)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:13]([C:25]([O:27][CH3:28])=[O:26])=[C:14]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[C:15]2=[CH:16][CH:17]=1)(=[O:9])=[O:10]

参加物

5

反応物 3

HCID 9845Trifluoroacetic anhydrideHCID 2733940GALLIUM(III) TRIFLUOROMETHANESULFONATEHCID 68866177HCID 68866177、化合物

生成物 1

HCID 68864572HCID 68864572、化合物収率 76.4%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
90 °C

実験手順

A solution of Example 510E (3.74 g, 9.13 mmol) in dichloroethane (183 mL) was treated with trifluoroacetic anhydride (2.58 mL, 18.3 mmol) and gallium (III) triflate (0.944 g, 1.83 mmol), stirred at 90° C. for 1.5 hours, and cooled to room temperature. The reaction was quenched with saturated aqueous sodium bicarbonate (200 mL), and the aqueous layer was extracted with CH2Cl2 (4×50 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography (7:3 hexanes/ethyl acetate) to provide the desired product (2.73 g, 76%). MS (ESI(+)) m/e 392 (M+H)+, 409 (M+NH4)+, 414 (M+Na)+; MS (ESI(−)) m/e 390 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.46 (br s, 1H), 7.74 (m, 2H), 7.52 (d, 1H), 7.43 (dd, 1H), 7.35 (td, 1H), 7.25 (d, 1H), 3.70 (s, 3H), 2.67 (t, 2H), 2.61 (m, 2H), 1.72 (m, 2H), 1.60 (m, 2H).

後処理

  1. temperaturecooled to room temperature
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate (200 mL)
  3. extractionthe aqueous layer was extracted with CH2Cl2 (4×50 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash chromatography (7:3 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-7b8b18f9400b4abe850cd9c8c69f045d
出典データセット
uspto-grants-2009_02
特許番号
US07491718B2

反応ノート

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