Ethyl chloroformate → HCID 86695275, 화합물

HRID 709412노트

반응식

HRID 709412 반응식
ClC(OCC)=O.[CH2:7]([O:9][C:10]([C:12]1[S:13][C:14]([C:17]([OH:19])=O)=[CH:15][N:16]=1)=[O:11])[CH3:8].[N-:20]=[N+:21]=[N-:22].[Na+]>CC(C)=O.O>[N:20]([C:17]([C:14]1[S:13][C:12]([C:10]([O:9][CH2:7][CH3:8])=[O:11])=[N:16][CH:15]=1)=[O:19])=[N+:21]=[N-:22]

참가 물질

6

반응물 3

HCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 667149792-(Ethoxycarbonyl)-1,3-thiazole-5-carboxylic acid2회

생성물 1

HCID 86695275HCID 86695275, 화합물수율 75.2%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

Ethyl chloroformate (9.8 g, 83.6 mmol) was added to a solution of 2-(ethoxycarbonyl)thiazole-5-carboxylic acid (Intermediate X, 13 g, 64.67 mmol), TEA (9.79 g, 97.01 mmol) in acetone (130 mL) at −20° C., stirred for 1 h, then a solution of NaN3 (5.4 g, 83.6 mmol) in water (15 mL) was added and stirred at RT for 30 mins. After completion, the solvent was evaporated, the crude residue was diluted with water (150 mL) and extracted with EtOAc (2×150 mL). The combined extracts were washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, filtered and evaporated to afford Ethyl 5-(azidocarbonyl)thiazole-2-carboxylate (11 g crude) as brown liquid. The crude was carried to next step without further purification.

후처리

  1. stirringstirred at RT for 30 mins
  2. customAfter completion, the solvent was evaporated
  3. additionthe crude residue was diluted with water (150 mL)
  4. extractionextracted with EtOAc (2×150 mL)
  5. washThe combined extracts were washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-a5a4cd7d3c9d4c828b014b773f3378a2
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181198B2

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