Triethylamine → HCID 11582303, 화합물

HRID 1713037

반응식

HRID 1713037 반응식
C(O[C:4]([C:6]1[NH:10][C:9]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[O:13][C:8]=2[CH:7]=1)=[O:5])C.[CH2:23]([O:25][C:26](=[O:54])[CH:27](CC)[CH2:28][CH2:29][N:30]1C(=S)N2C3C=C(C4C=CC([N+]([O-])=O)=CC=4)OC=3C=C2[C:31]1=[O:51])[CH3:24].N(CCCC(OCC)=O)=C=O.C(N(CC)CC)C.N(CCCC([O-])=O)=C=O>C(OCC)(=O)C.CCCCCC>[CH2:23]([O:25][C:26](=[O:54])[CH2:27][CH2:28][CH2:29][N:30]1[C:31](=[O:51])[N:10]2[C:9]3[CH:11]=[C:12]([C:14]4[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=4)[O:13][C:8]=3[CH:7]=[C:6]2[C:4]1=[O:5])[CH3:24]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 3445674Ethyl 4-isocyanatobutyrateHCID 594634452-(4-nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl esterHCID 86618327HCID 86618327, 화합물HCID 86618337HCID 86618337, 화합물

생성물 1

HCID 11582303HCID 11582303, 화합물수율 74%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

2-(4-Nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester (25 mg, 0.087 mmol, 1 molequivalent), prepared as described hereinabove (see, preparation of Compound 1), ethyl 4-isocyanatobutyrate (135 mg, 0.87 mmol) and triethylamine (214 μl, 1.74 mmol) were stirred overnight at room temperature. Additional 4-isocyanatobutyrate (130 μl) was added and the mixture was heated to 50° C. and was stirred at this temperature overnight. Once TLC analysis, using a 2:1 hexane:ethyl acetate mixture as eluent, indicated a complete conversion, the crude mixture was purified by column chromatography using a gradient of hexane to hexane:ethyl acetate (9:1) as eluent to give pure Compound 30 (26 mg, 74% yield).

후처리

  1. temperaturethe mixture was heated to 50° C.
  2. stirringwas stirred at this temperature overnight
  3. customthe crude mixture was purified by column chromatography

출처 및 근거

ORD 기록
ord-e4a13dcc3813461088139e50413ed0c5
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795255B2

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