1-Hydroxybenzotriazole → (1R,2R)-2-(4-{[acetyl(2-pyridinyl)amino]methyl}phenyl)-N-[(1S)-2-amino-2-oxo-1-phenylethyl]cyclohexanecarboxamide

HRID 480033

反応式

HRID 480033 の反応式
[C:1]([N:4]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[C:24]([OH:26])=O)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[NH2:27][C@@H:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:29]([NH2:31])=[O:30].ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O.C(N(CC)CC)C>[NH3:4].[C:1]([N:4]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[C:24]([NH:27][C@@H:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]([NH2:31])=[O:30])=[O:26])=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

参加物

9

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 729986(S)-(+)-2-Phenylglycine amideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59111308(1R,2R)-2-(4-{[Acetyl(2-pyridinyl)amino]methyl}phenyl)cyclohexanecarboxylic acid

生成物 2

HCID 222AmmoniaHCID 10227912(1R,2R)-2-(4-{[acetyl(2-pyridinyl)amino]methyl}phenyl)-N-[(1S)-2-amino-2-oxo-1-phenylethyl]cyclohexanecarboxamide収率 128.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

(1R,2R)-2-(4-{[Acetyl(2-pyridinyl)amino]methyl}phenyl)cyclohexanecarboxylic acid (0.44 g) is suspended in DMF (15 ml), (2S)-2-amino-2-phenylethanamide (0.37 g), triethylamine (0.68 ml), 1-hydroxybenzotriazole (0.18 g) and EDC hydrochloride (0.27 g) are admixed and the mixture is stirred at room temperature for 2 days. The suspension is diluted with water and extracted with dichloromethane and the organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated. Chromatography (silica gel, dichloromethane:methanol:saturated aqueous ammonia solution=50:1:0.05 to 20:1:0.05 gives (1R,2R)-2-(4-{[acetyl(2-pyridinyl)amino]methyl}phenyl)-N-[(1S)-2-amino-2-oxo-1-phenylethyl]cyclohexanecarboxamide (0.39 g) as a colourless solid.

後処理

  1. extractionextracted with dichloromethane
  2. washthe organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-c10c11c5509b4f82810cdfa64f99abec
出典データセット
uspto-grants-2003_11
特許番号
US06649616B2

関連ノート

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