Dicyclohexylcarbodiimide → 2-(3-(Benzyloxy)-2-ethyl-4-oxopyridin-1(4H)-yl)ethyl 5-(benzyloxycarbonylamino)-4-oxopentanoate

HRID 526672ノート

反応式

HRID 526672 の反応式
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][OH:18])[C:10]=1[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:28][C:29]([NH:31][CH2:32][C:33](=[O:39])[CH2:34][CH2:35][C:36](O)=[O:37])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:21]([O:28][C:29]([NH:31][CH2:32][C:33](=[O:39])[CH2:34][CH2:35][C:36]([O:18][CH2:17][CH2:16][N:11]1[CH:12]=[CH:13][C:14](=[O:15])[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]1[CH2:19][CH3:20])=[O:37])=[O:30])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 113691045-(((Benzyloxy)carbonyl)amino)-4-oxopentanoic acidHCID 149562853-Benzyloxy-2-ethyl-1-(2-hydroxyethyl)pyridin-4-one

生成物 1

HCID 900688162-(3-(Benzyloxy)-2-ethyl-4-oxopyridin-1(4H)-yl)ethyl 5-(benzyloxycarbonylamino)-4-oxopentanoate収率 87%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

4-(Dimethylamino)pyridine (3.3 mg, 0.0274 mmol) was added to a stirred solution of 3-(benzyloxy)-2-ethyl-1-(2-hydroxyethyl)pyridin-4(1H)-one (6) (149 mg, 0.547 mmol), 5-(benzyloxycarbonylamino)-4-oxopentanoic acid (5) (145 mg, 0.547 mmol) and N,N′-dicyclohexylcarbodiimide (118 mg, 0.574 mmol) in dichloromethane (8 mL). After 24 h, the resulting suspension was filtered through cotton wool, eluting with dichloromethane. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on silica gel, eluting with ethyl acetate then methanol, to give the title compound 7 (247 mg, 87%) as a colourless oil, RF 0.7 (MeOH); δH (300 MHz; CDCl3) 7.46-7.20 (11H, m, Ar and Pyr 6-H), 6.40 (1H, d, J 9.0 Hz, Pyr 5-H), 5.97 (1H, br s, NH), 5.22 (2H, s, PhCH2), 5.09 (2H, s, PhCH2), 4.22 (2H, t, J 6.0 Hz, OCH2CH2), 4.10-3.95 (4H, m, HNCH2 and OCH2CH2), 2.71-2.50 (6H, m, CH3CH2 and C(O)CH2CH2) and 0.99 (3H, t, J 7.0 Hz, CH3) δC (75 MHz; CDCl3) 204.7, 174.3, 172.3, 156.9, 146.2, 139.4, 138.0, 136.8, 129.1, 128.9, 128.8, 128.7, 128.5, 128.4, 128.3, 117.8, 73.3, 67.3, 63.3, 51.5, 50.9, 34.4, 27.9, 19.8 and 13.5.

後処理

  1. filtrationthe resulting suspension was filtered through cotton wool
  2. washeluting with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography on silica gel
  5. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-9f0f8478c9bb409c9284d72acb72beab
出典データセット
uspto-grants-2016_05
特許番号
US09346758B2

反応ノート

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