Dimethylformamide → HCID 69892327, 화합물

HRID 2289220노트

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HRID 2289220 반응식
[C:1]([O:5][C:6](NC1C=C(C(O)=O)N(C)C=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35]Br)=[CH:31][CH:30]=1)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C([N:41]([CH:44]([CH3:46])C)[CH2:42][CH3:43])(C)C.CN(C=[O:51])C>>[CH2:18]([O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][O:51][C:44]2[NH:41][CH:42]=[CH:43][CH:46]=2)=[CH:31][C:30]=1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27356364-[(tert-Butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acidHCID 541935972-Oxo-2-phenylethyl 4-(bromomethyl)benzoate

생성물 1

HCID 69892327HCID 69892327, 화합물수율 97%

실험 절차

A solution of Boc-pyrrole-OH (8)(2.9 g 12 mmol), 4-(bromomethyl)benzoic acid phenacyl ester (22) (4 g, 12 mmol) and diisopropylethylamine (3.0 ml, 16.8 mmol) in 60 ml of DMF were stirred at 50° C. for 6 hours. The solution was cooled and partitioned between 400 ml of water and 400 ml of ethyl ether. The ether layer was washed with (2×200 ml each) of 10% citric acid, brine, saturated sodium bicarbonate and brine. The organic phase was dried with sodium sulfate and concentrated in vacuo to yield compound 38 as light white foam which was used without further purification (5.4 g, 97% yield). TLC (2:3 hexane/ethyl acetate) Rf 0.6; 1H NMR (DMSO-d6) δ 9.14 (s, 1H), 8.03 (m, 4H), 7.67 (m, 1H), 7.55 (m, 4H), 7.13 (s, 1H), 6.72 (d, 1H, J=1.5 Hz), 5.74 (s, 1H), 5.32 (s, 1H), 3.79 (s, 3H), 1.42 (s, 9H); 13C NMR (DMSO-d6) δ 193.2, 165.5, 160.4, 153.2, 143.1, 134.5, 130.1, 129.5, 128.3, 128.2, 123.8, 120.3, 118.8, 108.2, 79.1, 67.7, 64.6, 36.7, 28.6.

후처리

  1. temperatureThe solution was cooled
  2. custompartitioned between 400 ml of water and 400 ml of ethyl ether
  3. washThe ether layer was washed with (2×200 ml each) of 10% citric acid, brine, saturated sodium bicarbonate and brine
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-546485e9743d48f8bca0d6c55d52dc6f
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06090947

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