1-Hydroxybenzotriazole → 5-Fluoro-4-hydroxy-3-{2-[(1H-imidazole-2-carbonyl)-amino]-propionylamino}-pentanoic acid tert-butyl ester

HRID 491970ノート

反応式

HRID 491970 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=O)=[O:7].[C:14]([O:18][C:19](=[O:27])[CH2:20][CH:21]([NH2:26])[CH:22]([OH:25])[CH2:23][F:24])([CH3:17])([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C1COCC1.CN(C1C=CN=CC=1)C>[C:14]([O:18][C:19](=[O:27])[CH2:20][CH:21]([NH:26][C:10](=[O:12])[CH:9]([NH:8][C:6]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[O:7])[CH3:13])[CH:22]([OH:25])[CH2:23][F:24])([CH3:17])([CH3:15])[CH3:16]

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 108566723-Amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl esterHCID 57462012(2S)-2-[(1H-imidazole-2-carbonyl)-amino]-propionic acid

生成物 1

HCID 670587205-Fluoro-4-hydroxy-3-{2-[(1H-imidazole-2-carbonyl)-amino]-propionylamino}-pentanoic acid tert-butyl ester収率 97%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (2S)-2-[(1H-imidazole-2-carbonyl)-amino]-propionic acid and 3-amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester (0.254 g) in THF (7 mL) was cooled to 0° C. before addition of DMAP (0.151 g), diisopropylethyl amine (0.56 mL), HOBT (0.16 g) and EDC HCl (0.23 g). The reaction mixture was stirred at ambient temperature for 18 hrs before being concentrated at reduced pressure. The residue was purified by silica gel chromatography (5% methanol in dichloromethane) to afford the sub-title compound as a colourless solid (0.386 g, 97%): 1H NMR 400 MHz CDCl3/CD3OD 1.40 (12H, m), 3.92 (1H, m), 4.20-4.55 (4H, m), 7.11 (2H, d, J 15); 19F NMR CDCl3-229.74 (m), −229.84 (m), −230.54 (m), −230.87 (m).

後処理

  1. concentrationbefore being concentrated at reduced pressure
  2. customThe residue was purified by silica gel chromatography (5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-299548a2bc08420fa7720f524516d7bf
出典データセット
uspto-grants-2009_05
特許番号
US07531570B2

反応ノート

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