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

HRID 2240857
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HRID 2240857 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b70300da569e437ba73c23a67c86989b
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723385B2

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