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

HRID 1809983노트

반응식

HRID 1809983 반응식
[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]([CH3:19])(C)[C:15]([OH:17])=[O:16].[CH:20](N(C(C)C)CC)(C)[CH3:21]>CO.O>[CH2:20]([O:17][C:15](=[O:16])[C:14]([CH3:19])([CH3:13])[CH2:2][S:1][C:4]1[S:8][C:7]([NH2:9])=[N:6][CH:5]=1)[CH3:21]

참가 물질

7

반응물 4

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

생성물 1

HCID 574814293-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

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) 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. The residue was stirred with ethanol, filtered, washed with ethanol and dried in a vacuum oven at 40° C. to give 3-(2-amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester.

후처리

  1. stirringthe reaction stirred overnight at room temperature
  2. concentrationpartially concentrated in vacuo and 5% citric acid
  3. additionwas added until pH 4
  4. filtrationThe brown precipitate was filtered
  5. washwashed with water and acetonitrile
  6. customdried over night at room temperature
  7. stirringThe residue was stirred with ethanol
  8. filtrationfiltered
  9. washwashed with ethanol
  10. customdried in a vacuum oven at 40° C.

출처 및 근거

ORD 기록
ord-4f57f6ac661c4db8b1875863225215d3
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362049B2

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