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

HRID 491970노트

반응식

HRID 491970 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-299548a2bc08420fa7720f524516d7bf
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531570B2

반응 노트

불러오는 중…