1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[(2-Phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acid

HRID 632933노트

반응식

HRID 632933 반응식
[C:1]1([C:7]2[O:8][C:9]([C:15]([F:18])([F:17])[F:16])=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.[NH2:30][CH2:31][CH2:32][C:33]([O:35]C)=[O:34].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C>ClCCl.C([O-])(O)=O.[Na+]>[C:1]1([C:7]2[O:8][C:9]([C:15]([F:18])([F:17])[F:16])=[C:10]([C:12]([NH:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:14])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 192794Methyl beta-alanateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acid

생성물 1

HCID 1179201883-[(2-Phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acid수율 103.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

2-phenyl-5-trifluoromethyloxazole-4-carboxylic acid (200 mg, 0.78 mmol), EDCI (372.7 mg, 1.94 mmol), methyl 3-aminopropionate (16.7 mg, 1.17 mmol), HOBt (157.6 mg, 1.17 mmol) and ethyldiisopropylamine (352.6 mg, 2.7 mmol) dissolved in dichloromethane (15 mL) were stirred for 24 hours. The reaction mixture was diluted with aqueous NaHCO3 and extracted with dichloromethane. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography to obtain the desired compound (265 mg, 99%) as a white solid.

후처리

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1e74dbaceb8f4781849c511d30a26ad9
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321728B2

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