Diisopropylethylamine → 3-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid

HRID 1095420ノート

反応式

HRID 1095420 の反応式
[S:1]([C:4]1[S:8][C:7]([NH2:9])=[N:6][CH:5]=1)[C:2]#N.[BH4-].[Na+].Br[CH2:13][C:14](C)([CH3:18])[C:15]([OH:17])=[O:16].C(N(C(C)C)CC)(C)C>CO.O>[NH2:9][C:7]1[S:8][C:4]([S:1][CH2:2][C:14]([CH3:18])([CH3:13])[C:15]([OH:17])=[O:16])=[CH:5][N:6]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2719323-Bromo-2,2-dimethylpropanoic acidHCID 3109677[(2-Amino-1,3-thiazol-5-yl)sulfanyl]formonitrileHCID 4311764Sodium borohydride

生成物 1

HCID 866378793-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

実験手順

5-thiocyanato-thiazol-2-ylamine (15.7 g) was dissolved in degassed methanol and sodium borohydride (4.5 g) in MeOH was added in one portion. The reaction was stirred for 30 min and 3-bromo-2,2-dimethyl-propionic acid (27 g) (prepared in the same manner as described by Greene at al, J Am Chem Soc 1955, 77, 3016) and diisopropylethylamine (17 mL) was added and the reaction stirred overnight at room temperature. The reaction was diluted with water, partially concentrated in vacuo and 5% citric acid was added until pH 4. The brown precipitate was filtered, washed with water and acetonitrile, and dried over night at room temperature to give 3-(2-amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid as light brown crystals.

後処理

  1. additionwas added
  2. stirringthe reaction stirred overnight at room temperature
  3. concentrationpartially concentrated in vacuo and 5% citric acid
  4. additionwas added until pH 4
  5. filtrationThe brown precipitate was filtered
  6. washwashed with water and acetonitrile
  7. customdried over night at room temperature

出典と根拠

ORDレコード
ord-62ccf8b955ed494a87c5a59bef0e509e
出典データセット
uspto-grants-2012_03
特許番号
US08138185B2

反応ノート

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