Acetic Acid → HCID 67113605、化合物

HRID 1924265

反応式

HRID 1924265 の反応式
CC1C=CC(S([N:11]2[CH:15]=[C:14]([CH:16]=O)[CH:13]=[N:12]2)(=O)=[O:9])=CC=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([OH:28])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.O.O>[OH2:9].[NH:11]1[CH:15]=[C:14]([CH2:16][N:18]2[C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:25][C:26]2=[O:28])[CH:13]=[N:12]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5837762-Aminophenylacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 577430311-tosyl-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 67113605HCID 67113605、化合物収率 8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

In a 100 ml, three-necked flask fitted with a magnetic stirrer, 1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carbaldehyde x58 (1.65 g, 6.6 mmol) is dissolved in a 1/1 mixture of THF/H2O (50 ml) and the solution containing (2-aminophenyl)acetic acid x96 (1 g, 66 mmol) is added. The pH is adjusted to 5 with acetic acid and the mixture is cooled to 0° C. Sodium triacetoxyborohydride (2.10 g, 10 mmol) is added and the mixture is stirred overnight at room temperature. Water is added and the aqueous phase is extracted three times with CH2Cl2. The combined organic phases are washed with brine, dried over MgSO4 and evaporated. Purification of the residue by preparative chromatography on silicagel and recrystallization from AcOEt affords 106 mg of pure 1-(1H-pyrazol-4-ylmethyl)-1,3-dihydro-2H-indol-2-one hydrate 173.

後処理

  1. customIn a 100 ml, three-necked flask fitted with a magnetic stirrer
  2. additionis added
  3. extractionthe aqueous phase is extracted three times with CH2Cl2
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customPurification of the residue by preparative chromatography
  8. customon silicagel and recrystallization from AcOEt

出典と根拠

ORDレコード
ord-a0ecb6dfa19a49b988dcfc199e8c3588
出典データセット
uspto-grants-2012_05
特許番号
US08178533B2

関連ノート

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