Acetic Acid → 1-[(3-{5-[3-Cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-pyrrolidinecarboxylic acid

HRID 1942750노트

반응식

HRID 1942750 반응식
[CH2:1]([C:3]1[C:8]([CH:9]=O)=[CH:7][CH:6]=[CH:5][C:4]=1[C:11]1[S:15][C:14]([C:16]2[CH:17]=[CH:18][C:19]([CH2:24][CH:25]([CH3:27])[CH3:26])=[C:20]([CH:23]=2)[C:21]#[N:22])=[N:13][N:12]=1)[CH3:2].[NH:28]1[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=[O:34])[CH2:29]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[C:21]([C:20]1[CH:23]=[C:16]([C:14]2[S:15][C:11]([C:4]3[C:3]([CH2:1][CH3:2])=[C:8]([CH2:9][N:28]4[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=[O:34])[CH2:29]4)[CH:7]=[CH:6][CH:5]=3)=[N:12][N:13]=2)[CH:17]=[CH:18][C:19]=1[CH2:24][CH:25]([CH3:27])[CH3:26])#[N:22]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 30346453-Pyrrolidinecarboxylic acidHCID 5049666Sodium triacetoxyborohydrideHCID 866590005-[5-(2-Ethyl-3-formylphenyl)-1,3,4-thiadiazol-2-yl]-2-(2-methylpropyl)benzonitrile

생성물 1

HCID 545773711-[(3-{5-[3-Cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-pyrrolidinecarboxylic acid수율 43.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 5-[5-(2-ethyl-3-formylphenyl)-1,3,4-thiadiazol-2-yl]-2-(2-methylpropyl)benzonitrile (D27) (100 mg, 0.266 mmol) in Ethanol (10 mL) stirred at room temperature was added 3-pyrrolidinecarboxylic acid (123 mg, 1.065 mmol) and AcOH (0.15 mL, 2.62 mmol). The reaction mixture was stirred at room temperature for 10 min, and sodium triacetoxyborohydride (110 mg, 0.522 mmol) was added. The reaction mixture was continuously stirred overnight. The reaction was quenched with water, and EtOH was evaporated in vacuo. The mixture was extracted by EA for 3 times. The combined organic solution was washed by brine, dried over anhydrous Na2SO4. The dried solution was filtered and concentrated, and purified by Mass Directed AutoPrep to afford 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-pyrrolidinecarboxylic acid (E48) (55 mg) as a off-white solid.

후처리

  1. waitThe reaction mixture was continuously stirred overnight
  2. customThe reaction was quenched with water, and EtOH
  3. customwas evaporated in vacuo
  4. extractionThe mixture was extracted by EA for 3 times
  5. washThe combined organic solution was washed by brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationThe dried solution was filtered
  8. concentrationconcentrated
  9. custompurified by Mass Directed AutoPrep

출처 및 근거

ORD 기록
ord-13dcf796eff04ea3b012885e50266c2b
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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