1-Hydroxybenzotriazole → 1-[trans-4-(N-tert-Butoxycarbonylglycylamino)-N-tert-Butoxycarbonyl-L-Prolyl]4-(4-Phenylbutanoyl)piperazine

HRID 2185473ノート

反応式

HRID 2185473 の反応式
Cl.CN(C)CCCN=C=NCC.[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]([NH:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:27]([C:37](O)=[O:38])[CH2:26]1)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:40]1([CH2:46][CH2:47][CH2:48][C:49]([N:51]2[CH2:56][CH2:55][N:54](C([O-])=O)[CH2:53][CH2:52]2)=[O:50])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.ON1C2C=CC=CC=2N=N1>ClCCl.C(N(CC)CC)C>[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]([NH:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])[C@H:27]([C:37]([N:54]2[CH2:55][CH2:56][N:51]([C:49](=[O:50])[CH2:48][CH2:47][CH2:46][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:52][CH2:53]2)=[O:38])[CH2:26]1)=[O:23])=[O:19])([CH3:15])([CH3:16])[CH3:14]

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21341559trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-prolineHCID 224587744-(4-Phenylbutanoyl)l-piperazinecarboxylate

生成物 1

HCID 701756021-[trans-4-(N-tert-Butoxycarbonylglycylamino)-N-tert-Butoxycarbonyl-L-Prolyl]4-(4-Phenylbutanoyl)piperazine収率 100.7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

Triethylamine (72 μL) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (98.9 mg) were added to a solution of trans-4-(N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-proline (Compound D103 (B), 144.9 mg), 4-(4-phenylbutanoyl)l-piperazinecarboxylate (B, 100 mg), and 1-hydroxybenzotriazole (65 mg) in dichloromethane at room temperature. After stirring at room temperature for 20 hr, the reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic layer was washed with saturated sodium hydrogen carbonate and brine. After drying over anhydrous sodium sulfate, the organic layer was evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 20:1) to give the titled compound (220 mg) as a white powder: 1H-NMR(400 MHz, CDCl3) δ 1.46 (s, 18H), 1.99 (t, 2H), 2.33 (m, 2H), 2.69 (t, 2H), 3.39-3.85 (m, 13H), 7.18-7.31(m, 5H).

後処理

  1. customthe reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid
  2. washThe organic layer was washed with saturated sodium hydrogen carbonate and brine
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe organic layer was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 20:1)

出典と根拠

ORDレコード
ord-7680b2d3fe0341098b38d11cabbb514b
出典データセット
uspto-grants-2002_06
特許番号
US06399629B1

反応ノート

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