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

HRID 860656

反応式

HRID 860656 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-338aec2812614684ac8e8c1399c4944c
出典データセット
uspto-grants-2006_12
特許番号
US07153878B2

関連ノート

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