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Trifluoroacetic acid → N-[4-Cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycine

HRID 2109072
ノート
印刷プレビュー

反応式

HRID 2109072 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])=[CH:5][C:4]=1[C:22]([F:25])([F:24])[F:23])#[N:2].C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][CH:19]2[CH2:20][CH2:21]2)[CH2:10][C:11]([OH:13])=[O:12])=[CH:5][C:4]=1[C:22]([F:23])([F:25])[F:24])#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 113142081,1-Dimethylethyl N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycinate

生成物 1

HCID 11369986N-[4-Cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycine収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1,1-dimethylethyl N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycinate (5.01 g, 14.1 mmol), TFA (50 mL), and triethylsilane (5 mL) in CH2Cl2 (50 mL) was stirred at ambient temperature for 3 h. When the TLC indicated no remaining starting material, the solvents were removed under reduced pressure, and the residue was stirred in hexane (50 mL) for 12 hours. The solid precipitate was filtered and dried to obtain 2.9 g (71%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.61 (d, J=8.8 Hz, 1H), 6.97 (d, J=2.8 Hz, 1H), 6.78 (dd, J=8.8, 2.8 Hz, 1H), 4.29 (s, 2H), 3.34 (d, J=6.4 Hz, 2H), 1.37 (m, 1H), 0.64 (m, 2H), 0.27 (m, 2H).

後処理

  1. customthe solvents were removed under reduced pressure
  2. stirringthe residue was stirred in hexane (50 mL) for 12 hours
  3. filtrationThe solid precipitate was filtered
  4. customdried

出典と根拠

ORDレコード
ord-f3c12380df1d4f4580b5d24a61ac5daf
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07514470B2

反応ノート

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