2-Methyl-2-butene → 2-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acid

HRID 1037961노트

반응식

HRID 1037961 반응식
[CH:1]([C:3]1[S:7][C:6]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[N:5][CH:4]=1)=[O:2].O.O.P([O-])(O)(O)=[O:21].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.O>[C:13]([O:12][C:11]([NH:10][CH:8]([C:6]1[S:7][C:3]([C:1]([OH:21])=[O:2])=[CH:4][N:5]=1)[CH3:9])=[O:17])([CH3:16])([CH3:15])[CH3:14]

참가 물질

7

반응물 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 86657335Tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamate

생성물 1

HCID 673960092-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acid수율 61.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

A mixture of tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamate (3.5 g, 0.014 mol), sodium dihydrogen phosphate dihydrate (2.9 g, 0.019 mol) and 2-methyl-2-butene (3.85 g, 0.055 mol) in tert-butyl alcohol (70 ml) and water (40 mL) was stirred at room temperature for 30 minutes. Sodium chlorite (3.22 g, 0.035 mol) was added and the reaction maintained at room temperature for an additional 2 hours. The reaction was concentrated, diluted with water (50 mL) and acidified (pH=4) with the addition of 3N H3PO4. The mixture was extracted with DCM, the organic layer dried over anhydrous Na2SO4 and evaporated to dryness to afford 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylic acid (2.35 g, 60%). LC-MS: (FA) ES+ 273.

후처리

  1. temperaturethe reaction maintained at room temperature for an additional 2 hours
  2. concentrationThe reaction was concentrated
  3. additiondiluted with water (50 mL)
  4. additionwith the addition of 3N H3PO4
  5. extractionThe mixture was extracted with DCM
  6. dry with materialthe organic layer dried over anhydrous Na2SO4
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-4b6996706a9343d78ed403f833a97e5e
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546588B2

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