1-Hydroxybenzotriazole → N-tert-Butoxycarbonyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide

HRID 2185404노트

반응식

HRID 2185404 반응식
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]([NH:33][C:34](=[O:48])[C@@H:35]2[CH2:39][C@@H:38]([NH2:40])[CH2:37][N:36]2[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH:24]=1.[OH:49][C@H:50]([CH2:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:51](O)=[O:52]>ClCCl.C(Cl)(Cl)Cl>[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]([NH:33][C:34](=[O:48])[C@@H:35]2[CH2:39][C@@H:38]([NH:40][C:51](=[O:52])[C@H:50]([OH:49])[CH2:54][CH2:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[CH2:37][N:36]2[C:41]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:42])[CH:24]=1

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2759328(R)-2-Hydroxy-4-phenylbutyric acidHCID 70173042trans-4-Amino-N-tert-Butoxycarbonyl-L-Proline 3-Quinolylamide

생성물 1

HCID 70173053N-tert-Butoxycarbonyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide수율 97.8%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

1-Hydroxybenzotriazole (147 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (766 mg) were added to a stirred solution of trans-4-amino-N-tert-butoxycarbonyl-L-proline 3-quinolylamide(E, 1.30 g) and (R)-2-hydroxy-4-phenylbutanoic acid (F, 720 mg) in dichloromethane (40 mL) at 0° C. The mixture was stirred at room temperature overnight. The reaction mixture was diluted with chloroform and washed with saturated sodium hydrogen carbonate and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=100:1, v/v) to give the title compound (1.85 g) as a colorless foam: 1H NMR (400 MHz, CDCl3) δ 1.45 (m, 9H), 1.70 (m, 2H), 1.94 (m, 1H), 2.15 (m, 1H), 2.75 (m, 2H), 3.29 (m, 1H), 3.80 (m, 1H), 4.11 (m, 1H), 4.53 (m, 1H), 4.60 (m, 1H), 6.76 (m, 1H), 7.15-7.26 (m, 5H), 7.48 (m, 1H), 7.57 (m, 1H), 7.73 (m, 1H), 7.95 (d, J=16.8 Hz, 1H), 8.68 (s, 1H), and 8.69 (s,1H).

후처리

  1. washwashed with saturated sodium hydrogen carbonate and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (chloroform

출처 및 근거

ORD 기록
ord-31a064d2fdbb470389af30b74b953efe
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06399629B1

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