Triethylamine → HCID 178439611, 화합물

HRID 54856

반응식

HRID 54856 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.FC1C(O)=C(F)C(F)=C(F)C=1F.CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl.Cl.[NH2:62][CH2:63][CH2:64][C:65]1[N:69]=[CH:68][NH:67][CH:66]=1>C(OCC)(=O)C.CN(C)C=O>[NH:67]1[CH:66]=[C:65]([CH2:64][CH2:63][NH:62][C:26](=[O:27])[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)([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[CH3:29])[N:69]=[CH:68]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 148025032-adamantyloxycarbonyl-alpha-methyl-DL-tryptophanHCID 178478691HCID 178478691, 화합물

생성물 1

HCID 178439611HCID 178439611, 화합물수율 47.3%

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 (6 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added pentafluorophenol (0.189 g, 1.03 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.200 g, 1.04 mmol). This mixture was stirred 2 hours, then triethylamine (0.36 mL, 2.6 mmol) and histamine dihydrochloride (0.240 g, 1.30 mmol) were added. After stirring an additional 40 hours, the resulting mixture was diluted with ethyl acetate (20 mL), and washed with water. The organic phase was dried over MgSO4, concentrated, purified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 10% methanol/dichloromethane eluant), and dried for 48 hours under vacuum at 70° C. to provide 0.234 g (47%) of product; 1H NMR (CDCl3) δ1.40-1.60 (2H, m), 1.57 (3H, s), 1.65-2.00 (13H, m), 2.65-2.75 (2H, m), 3.25-3.45 (4H, m), 4.82 (1H, br s), 5.42 ([H, br s), 6.67 (1H, s), 6.81 (1H, br s), 6.91 (1H, br s),7.00-7.20 (2H, m), 7.34 (1H, d, J 7 Hz), 7.46 (1H, s), 7.55 (1H, d, J 7 Hz), 8.67 (1H, br s).

후처리

  1. stirringAfter stirring an additional 40 hours
  2. washwashed with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 10% methanol/dichloromethane eluant)
  6. customdried for 48 hours under vacuum at 70° C.

출처 및 근거

ORD 기록
ord-85cef224fcff45b1b389493bd1530816
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622983

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