Diisopropylcarbodiimide → HCID 18923895, 화합물

HRID 1290253

반응식

HRID 1290253 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 18923895HCID 18923895, 화합물수율 90.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8778b93efd1b4216936f3ad614e754e3
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750724

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