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

HRID 1942749

反応式

HRID 1942749 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:25][CH3:26])=[C:19]([CH:22]=[CH:23][CH:24]=3)[CH:20]=O)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[NH:27]1[CH2:31][CH2:30][CH:29]([C:32]([OH:34])=[O:33])[CH2:28]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:25][CH3:26])=[C:19]([CH2:20][N:27]4[CH2:31][CH2:30][CH:29]([C:32]([OH:34])=[O:33])[CH2:28]4)[CH:22]=[CH:23][CH:24]=3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 30346453-Pyrrolidinecarboxylic acidHCID 5049666Sodium triacetoxyborohydrideHCID 58494009HCID 58494009、化合物

生成物 1

HCID 584940751-{[3-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-pyrrolidinecarboxylic acid収率 46.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylbenzaldehyde (100 mg, 0.258 mmol) (D11) in Ethanol (10 mL) stirred at room temperature was added 3-pyrrolidinecarboxylic acid (119 mg, 1.034 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/THF for 3 times. The combined organic solution was washed by brine, dried over anhydrous Na2SO4. The dried solution was filtered and concentrated, and dissolved in THF. The residue was purified by Mass Directed AutoPrep to afford 1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-pyrrolidinecarboxylic acid (E44) (58 mg) as a TFA salt (off-white solid).

後処理

  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/THF 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. dissolutiondissolved in THF
  10. customThe residue was purified by Mass Directed AutoPrep

出典と根拠

ORDレコード
ord-82e703db50864ff2bb331bd31758a038
出典データセット
uspto-grants-2013_03
特許番号
US08389508B2

関連ノート

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