Dimethylformamide → HCID 69892327、化合物

HRID 1841699ノート

反応式

HRID 1841699 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

HCID 69892327HCID 69892327、化合物収率 97%

実験手順

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), 7.5 (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.

後処理

  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

出典と根拠

ORDレコード
ord-87680d05c05941cc827ecc399822aea6
出典データセット
uspto-grants-2004_01
特許番号
US06683189B1

反応ノート

読み込み中…