Diisopropylcarbodiimide → HCID 18923895、化合物

HRID 1290253

反応式

HRID 1290253 の反応式
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][C:20](O)=O)C1C=CC=CC=1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[OH:44][C:45]1[CH:46]=[CH:47][C:48]2[O:53][CH2:52][CH:51]([CH2:54][NH2:55])[O:50][C:49]=2[CH:56]=1>CN(C=O)C>[OH:44][C:45]1[CH:46]=[CH:47][C:48]2[O:53][CH2:52][CH:51]([CH2:54][NH:55][CH2:20][CH2:19][CH2:18][C:12]3[C:11]4[C:15](=[CH:16][CH:17]=[C:9]([OH:8])[CH:10]=4)[NH:14][CH:13]=3)[O:50][C:49]=2[CH:56]=1

参加物

6

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 189238902,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine hydrochlorideHCID 189238923-[5-(Benzyloxy)-3-indolyl]propanoic Acid

生成物 1

HCID 18923895HCID 18923895、化合物収率 90.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

5-Benzyloxyindole-3-propionic acid (1.5 g, 5.0 mmole), 1-hydroxybenzotriazole hydrate (0.8 g, 6.0 mmole) and 1,3-diisopropylcarbodiimide (1.9 ml, 12.0 mmole) were combined in 150 ml of DMF and stirred at room temperature for 2 hours under a nitrogen atmosphere. To this was added dropwise 7-hydroxy-2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochloride (1.1 g, 5.0 mmole) in 50 ml of DMF and the mixture was further stirred for 48 hours. The solvent was removed and replaced with dichloromethane. The mixture was then washed with H2O. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was chromatographed on silica gel using ethyl acetate as eluant. Fractions containing product were concentrated and recrystallized from ethyl acetate to give 1.6 g (68%) of the desired product, (7-hydroxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-3-(5-hydroxy-1H-indol-3-yl)-propanamide, as a white solid.

後処理

  1. stirringthe mixture was further stirred for 48 hours
  2. customThe solvent was removed
  3. washThe mixture was then washed with H2O
  4. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was chromatographed on silica gel
  8. additionFractions containing product
  9. concentrationwere concentrated
  10. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-8778b93efd1b4216936f3ad614e754e3
出典データセット
uspto-grants-1998_05
特許番号
US05750724

関連ノート

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