3-Aminobenzoic Acid → 3-[(Trifluoroacetyl)amino]benzoic acid

HRID 1689984

반응식

HRID 1689984 반응식
O=C(C1C=CC=CC=1)C[O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH:7]=1.NC1C=C(C=CC=1)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[F:15][C:14]([F:16])([F:17])[C:13]([NH:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[C:5]([OH:19])=[O:4])=[O:18]

참가 물질

5

반응물 3

HCID 74193-Aminobenzoic AcidHCID 9845Trifluoroacetic anhydrideHCID 11593542-Oxo-2-phenylethyl 3-[(trifluoroacetyl)amino]benzoate3회

생성물 1

HCID 2838403-[(Trifluoroacetyl)amino]benzoic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A compound having general Formula 4, exemplified by 3-(2,2,2-Trifluoro-acetylamino)-benzoic acid 2-oxo-2-phenyl-ethyl ester (Compound 4; FIG. 1) can be prepared as follows. A solution of 3-aminobenzoic acid (137 mg, 1.0 mmol) in dichloromethane is treated with trifluoroacetic anhydride (420 mg, 2.0 mmol). The reaction mixture is stirred until no further reaction occurs. The reaction mixture is concentrated to give 3-(2,2,2-Trifluoro-acetylamino)-benzoic acid. A solution of 3-(2,2,2-Trifluoro-acetylamino)-benzoic acid (233 mg, 1.0 mmol) and 2-hydroxyacetophenone (136 mg, 1.0 mmol) in dimethylformamide and diisopropylethylamine (260 mg, 2.0 mmol) is treated with HBTU (379 mg, 1.0 mmol). The reaction mixture is stirred until no further reaction occurs. The reaction is poured into ethyl acetate and water. The organic phase is collected, dried and concentrated to give the title compound.

후처리

  1. customcan be prepared
  2. concentrationThe reaction mixture is concentrated

출처 및 근거

ORD 기록
ord-0ba912b5d57e40c5939d0f9521df302f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153645B2

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