Ethoxalyl chloride → Ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate

HRID 625795노트

반응식

HRID 625795 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].CCN(C(C)C)C(C)C.Cl[C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1COCC1>[C:4]([C:3]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=1[NH:1][C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:5])[NH2:6]

참가 물질

5

반응물 3

HCID 20884Ethoxalyl chlorideHCID 81531DiisopropylethylamineHCID 123748372-Amino-4-chlorobenzamide

생성물 1

HCID 66610703Ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-amino-4-chlorobenzamide (393 mg, 2.30 mmol) and DIEA (0.60 mL, 3.45 mmol) in THF (15 mL) at 0° C. was added ethyl chlorooxoacetate (0.28 mL, 2.53 mmol). The solution was allowed to warm to rt and stir for 2 h. The mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 10-50% EtOAc/hexanes to afford ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate as a solid (545 mg, 88%). 1H NMR (300 MHz, DMSO-d6) δ 1.32 (t, J=6.97 Hz, 3H), 4.31 (q, J=6.97 Hz, 2H), 7.34 (d, J=8.48 Hz, 1H), 7.86-8.03 (m, 2H), 8.44 (br s, 1H), 8.62 (s, 1H), 13.24 (s, 1H)

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 10-50% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-9b62e8f6826749d3b5261eed822d0a66
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09308207B2

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