Sulfuric Acid → [2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-acetic acid methyl ester

HRID 854550

반응식

HRID 854550 반응식
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH:5]([NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)=[O:11])[C:6](=O)[CH3:7].S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[N:9]=[C:10]([C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[O:11][C:6]=1[CH3:7]

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 877132023-[(6-Chloro-pyridine-3-carbonyl)-amino]-4-oxo-pentanoic acid methyl ester

생성물 1

HCID 58765666[2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-acetic acid methyl ester수율 22%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

반응 조건

온도
40 °C

실험 절차

3-[(6-Chloro-pyridine-3-carbonyl)-amino]-4-oxo-pentanoic acid methyl ester is dissolved in acetic anhydride (75 mL) and concentrated sulfuric acid is added in 500 uL portions five times over a four hour period. The reaction is monitored by HPLC. The reaction is then heated to 40° C. until the starting material is consumed. The reaction is allowed to proceed at room temperature overnight. The reaction is then concentrated to dryness and purified by column chromatography. This procedure yielded (12.8 g, 48 mmol) 22% of the desired oxazole over four steps.

후처리

  1. customis consumed
  2. concentrationThe reaction is then concentrated to dryness
  3. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-973361e0cb97477593554eef8b429eaa
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259175B2

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