Oxalyl chloride → Ethyl 5-(3-(trifluoromethyl)benzyl)-1,2,4-oxadiazole-3-carboxylate

HRID 58606

반응식

HRID 58606 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.C(Cl)(=O)C(Cl)=O.[NH2:21][C:22](=[N:28]O)[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(N(CC)C(C)C)(C)C>ClCCl.N1C=CC=CC=1.CN(C=O)C>[F:13][C:2]([F:1])([F:14])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH2:9][C:10]1[O:12][N:28]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=1

참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 676953-(Trifluoromethyl)benzeneacetic acidHCID 81531DiisopropylethylamineHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

생성물 1

HCID 66832161Ethyl 5-(3-(trifluoromethyl)benzyl)-1,2,4-oxadiazole-3-carboxylate수율 4%

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

This compound was prepared according to general method 2 with (step I) 2-(3-(trifluoromethyl)phenyl)acetic acid (0.773 g; 3.78 mmol) and oxalyl chloride (0.352 mL; 4.16 mmol) in dichloromethane (12 mL) with few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino)acetate (0.5 g; 3.78 mmol) and N,N diisopropylethylamine (1.05 mL; 6.06 mmol) in dichloromethane (6 mL) and (step III) pyridine (18 mL). The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.040 g (4%) of ethyl 5-(3-(trifluoromethyl)benzyl)-1,2,4-oxadiazole-3-carboxylate as a white solid.

후처리

  1. customThis compound was prepared
  2. customThe crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-b52d720bc7124155aa8989ca832bdea6
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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