Acetic Acid → HCID 53704947、化合物

HRID 1609397ノート

反応式

HRID 1609397 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26](=[O:30])[C:27]([OH:29])=[O:28])=[CH:18]1.[F:31][C:32]1[C:37](O)=[C:36]([F:39])[C:35]([F:40])=[C:34]([F:41])[C:33]=1[F:42].C(O)(=O)C>O1CCCC1>[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26](=[O:30])[C:27]([O:29][C:37]2[C:36]([F:39])=[C:35]([F:40])[C:34]([F:41])=[C:33]([F:42])[C:32]=2[F:31])=[O:28])=[CH:18]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 4589028N-Methyl-3-indoleglyoxylic acid

生成物 1

HCID 53704947HCID 53704947、化合物収率 22%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

1.13 g (5.5 mol) of dicyclohexylcarbodiimide were added to a solution, cooled in ice, of 1 g (5 mmol) of 1-methylindole-3glyoxylic acid and 1.01 g (5 mmol) of pentafluorophenol in 50 ml of dry tetrahydrofuran. After stirring for 4 hours under a nitrogen atmosphere at 0° C., the mixture was allowed to warm to room temperature and left to stand for 60 hours. Then, 3 ml of glacial acetic acid were added and the mixture obtained was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using dichloromethane for the elution to give 404 mg (22%) of pentafluorophenyl 1-methylindole-3-glyoxylate in the form of a pale yellow solid of melting point 168°-9° C.

後処理

  1. temperatureto warm to room temperature
  2. waitleft
  3. waitto stand for 60 hours
  4. customthe mixture obtained
  5. filtrationwas filtered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel
  8. washfor the elution

出典と根拠

ORDレコード
ord-6811b0b444764a80a8ee0a479cd84ba1
出典データセット
uspto-grants-1995_03
特許番号
US05399712

反応ノート

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