N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → 5-Amino-4-[2-(tert-butoxycarbonylamino)acetyl]amino-1-(2-hydroxyethyl)pyrazole

HRID 1247798

반응식

HRID 1247798 반응식
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[N:9][N:10]([CH2:13][CH2:14][OH:15])[C:11]=1[NH2:12].[C:16]([O:20][C:21]([NH:23][CH2:24][C:25](ON1C(=O)CCC1=O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[NH2:12][C:11]1[N:10]([CH2:13][CH2:14][OH:15])[N:9]=[CH:8][C:7]=1[NH:6][C:25](=[O:26])[CH2:24][NH:23][C:21]([O:20][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:22]

참가 물질

5

반응물 3

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 81531DiisopropylethylamineHCID 116731484,5-Diamino-1-(2-hydroxyethyl)pyrazole sulfate

생성물 1

HCID 219045155-Amino-4-[2-(tert-butoxycarbonylamino)acetyl]amino-1-(2-hydroxyethyl)pyrazole수율 80.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 4,5-diamino-1-(2-hydroxyethyl)pyrazole sulfuric acid salt (1.20 g) and N-[2-(tert-butoxycarbonylamino)acetoxy]succinimide (1.35 g) in methylene chloride (20 ml) was added N-ethyldiisopropylamine (2.1 ml) under ice-cooling, and the mixture was stirred at room temperature for 17 hours. The reaction mixture was washed with water (40 ml), saturated aqueous sodium hydrogen carbonate solution (40 ml) and brine (40 ml). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The oily residue was purified by column chromatography on silica gel eluting with 10% methanol/chloroform to give 5-amino-4-[2-(tert-butoxycarbonylamino)acetyl]amino-1-(2-hydroxyethyl)pyrazole (1.20 g) as a solid.

후처리

  1. temperaturecooling
  2. washThe reaction mixture was washed with water (40 ml), saturated aqueous sodium hydrogen carbonate solution (40 ml) and brine (40 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by column chromatography on silica gel eluting with 10% methanol/chloroform

출처 및 근거

ORD 기록
ord-52dd1d3126c343a9b2cb3cf6af9914c6
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129232B2

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