Ethyl Acetate → HCID 21891719、化合物

HRID 720668ノート

反応式

HRID 720668 の反応式
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][C:7]=1[CH3:31])=[O:5])C.[OH-].[Na+].C(OCC)(=O)C>C(O)C.O>[CH3:31][C:7]1[N:8]=[C:9]([NH:11][C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:10][C:6]=1[C:4]([OH:5])=[O:3]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2 回HCID 58739232HCID 58739232、化合物

生成物 1

HCID 21891719HCID 21891719、化合物収率 11.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A mixture of 4-methyl-2-(trityl-amino)-thiazole-5-carboxylic acid ethyl ester (500 mg, 1.17 mmol) in ethanol (10 mL) at 25° C. was treated with a 1N aqueous sodium hydroxide solution (3.51 mL, 3.51 mmol). The resulting mixture was heated to 50° C. for 18 h. At this time, the reaction was treated with an additional amount of a 1N aqueous sodium hydroxide solution (3.6 mL, 3.6 mmol). This mixture was heated at 50° C. for an additional 8 days. At this time, the reaction was diluted with water (100 mL), acidified to pH=5, and treated with ethyl acetate. The resulting white solid was collected by filtration and dried in vacuo. The filtrate was extracted with ethyl acetate. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 4-methyl-2-(trityl-amino)-thiazole-5-carboxylic acid (55.7 mg, 11.9%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ9.09 (broad s, 1H), 7.22 (m, 15 H), 2.22 (s, 3H).

後処理

  1. temperatureThis mixture was heated at 50° C. for an additional 8 days
  2. filtrationThe resulting white solid was collected by filtration
  3. customdried in vacuo
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-02a5209054e24bbf8939a90205d1be0d
出典データセット
uspto-grants-2006_11
特許番号
US07135475B2

反応ノート

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