1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tricyclo[3.3.1.13,7]dec-2-yl (+/-)-[1-(1H-indol-3-ylmethyl)-1-methyl-2-[[2-(1-methyl-1H-pyrrol-2-yl) ethyl]amino]-2-oxoethyl]carbamate

HRID 54854

반응식

HRID 54854 반응식
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:12]([NH:14][C:15]([CH3:29])([C:26](O)=[O:27])[CH2:16][C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=1)=[O:13])[CH2:8]2.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[NH2:51][CH2:52][CH2:53][C:54]1[N:55]([CH3:59])[CH:56]=[CH:57][CH:58]=1>C(OCC)(=O)C.CN(C)C=O>[NH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([CH2:16][C:15]([NH:14][C:12](=[O:13])[O:11][CH:2]2[CH:1]3[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]2[CH2:4]4)[CH2:8]3)([CH3:29])[C:26]([NH:51][CH2:52][CH2:53][C:54]2[N:55]([CH3:59])[CH:56]=[CH:57][CH:58]=2)=[O:27])=[CH:18]1

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5650581-methyl-1H-pyrrole-2-ethylamineHCID 148025032-adamantyloxycarbonyl-alpha-methyl-DL-tryptophan

생성물 1

HCID 86747497Tricyclo[3.3.1.13,7]dec-2-yl (+/-)-[1-(1H-indol-3-ylmethyl)-1-methyl-2-[[2-(1-methyl-1H-pyrrol-2-yl) ethyl]amino]-2-oxoethyl]carbamate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0.401 g, 1.01 mmol) in dry ethyl acetate (4 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added 1-hydroxybenzotriazole (0.139 g, 1.03 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.199 g, 1.04 mmol). This mixture was stirred 2 hours and 0.16 g (1.3 mmole) of 2-(2-aminoethyl)-1-methylpyrrole was added. After stirring an additional 18 hours, the resulting mixture was diluted with ethyl acetate (20 mL), and washed with aqueous 1N citric acid, saturated aqueous sodium bicarbonate, and brine solutions. The organic phase was dried over MgSO4 and purified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 67% ethyl acetate/hexane eluant). Concentration followed by drying under vacuum for 48 hours at 60° C. provided 0.301 g (59%) at product; 1H NMR (CDCl3) δ1.49-1.60 (2H, m), 1.56 (3H, s), 1.70-2.00 (12H, m), 2.61 (2H, t, J 7 Hz), 3.23-3.55 (4H, m), 3.50 (3H, s), 4.82 (1H, br s), 5.20 (1H, br s), 5.76 (1H, br s), 6.00 (1H, t, J 3 Hz), 6.34 (1H, br s), 6.53 (1H, br s), 6.97 (1H, br s), 7.09-7.19 (2H, m), 7.36 (1H, d, J 8 Hz), 7.59 (1H, d, J 8 Hz), 8.16 (1H, br s).

후처리

  1. stirringAfter stirring an additional 18 hours
  2. washwashed with aqueous 1N citric acid, saturated aqueous sodium bicarbonate, and brine solutions
  3. dry with materialThe organic phase was dried over MgSO4
  4. custompurified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 67% ethyl acetate/hexane eluant)
  5. concentrationConcentration
  6. customby drying under vacuum for 48 hours at 60° C.
  7. customprovided 0.301 g (59%) at product

출처 및 근거

ORD 기록
ord-e3bc7f6f460e4e82abdc50db7acd260f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622983

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