Sodium Acetate → 2-(2-Aminothiazol-4-yl)-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)acetic acid

HRID 1088108ノート

反応式

HRID 1088108 の反応式
Br[CH2:2][C:3](=O)[C:4](=[N:8][O:9][CH2:10][C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])[C:5]([OH:7])=[O:6].[NH2:20][C:21]([NH2:23])=[S:22].C([O-])(=O)C.[Na+]>O1CCCC1.O>[NH2:23][C:21]1[S:22][CH:2]=[C:3]([C:4](=[N:8][O:9][CH2:10][C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])[C:5]([OH:7])=[O:6])[N:20]=1

参加物

6

反応物 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 538664824-Bromo-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyric acid

生成物 1

HCID 867391642-(2-Aminothiazol-4-yl)-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)acetic acid収率 18.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To a solution of 4-bromo-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyric acid (20 g) in tetrahydrofuran (50 ml) was added a solution of thiourea (3.9 g) and sodium acetate (4.2 g) in water (50 ml), and the mixture was stirred at 40° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure to half of the original volume, which was adjusted to pH 7.5 with a saturated aqueous sodium bicarbonate and then washed with ethyl acetate. After the aqueous solution was further adjusted to pH 2.0 with 10% hydrochloric acid, the water was removed by decantation. The residual substance was dissolved in tetrahydrofuran (200 ml), followed by drying over magnesium sulfate. Removal of the solvent gave an oil, which was triturated with diisopropyl ether to give 2-(2-aminothiazol-4-yl)-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)acetic acid (syn isomer) (3.5 g).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure to half of the original volume, which
  2. washwashed with ethyl acetate
  3. customthe water was removed by decantation
  4. dissolutionThe residual substance was dissolved in tetrahydrofuran (200 ml)
  5. dry with materialby drying over magnesium sulfate
  6. customRemoval of the solvent
  7. customgave an oil, which
  8. customwas triturated with diisopropyl ether

出典と根拠

ORDレコード
ord-2726c5d4c75f4b008536a74b32dd8719
出典データセット
uspto-grants-1990_10
特許番号
US04960889

反応ノート

読み込み中…