Dichloromethane → 2-{4-[2-Acetylamino-3-(4-fluorophenyl)propionyl]-3-cyclopropyl-methyl-2-oxo-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl propionamide

HRID 720172ノート

反応式

HRID 720172 の反応式
[NH2:1][CH:2]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[C:12]([NH:14][CH3:15])=[O:13])[C:7](=[O:27])[CH:6]1[CH2:28]C1CC1)=[O:4].C(N([CH2:45][CH3:46])CC)C.[C:47](Cl)(=[O:49])[CH3:48].[CH2:51](Cl)Cl>>[C:47]([NH:1][CH:2]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[C:12]([NH:14][CH3:15])=[O:13])[C:7](=[O:27])[C:6]1([CH3:28])[CH:46]1[CH2:45][CH2:51]1)=[O:4])(=[O:49])[CH3:48]

参加物

5

反応物 4

HCID 6344Dichloromethane2 回HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 102564532-[4-[2-amino-3-(4-fluorophenyl)-propionyl]-3-cyclopropylmethyl-2-oxo-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl-propionamide

生成物 1

HCID 865959292-{4-[2-Acetylamino-3-(4-fluorophenyl)propionyl]-3-cyclopropyl-methyl-2-oxo-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl propionamide

実験手順

To a solution of 2-[4-[2-amino-3-(4-fluorophenyl)-propionyl]-3-cyclopropylmethyl-2-oxo-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl-propionamide, 18, (100 mg, 0.155 mmol) and triethylamine (20 mg, 0.2 mmole) in CH2Cl2 (5 mL) at 0° C. is added dropwise acetyl chloride (13.4 mg, 0.17 mmole). The reaction is allowed to warm to room temperature and stirred 1 hour. The reaction is diluted with CH2Cl2 (10 mL) and extracted with water then brine, dried and concentrated in vacuo to afford a residue which is purified over silica gel to afford the desired product. 13C NMR (CDCl3, 75 MHz), 170.12, 169.90, 169.82, 169.49, 169.35, 167.70, 134.07, 133.67, 132.57, 131.64, 128.65, 127.83, 127.80, 127.70, 127.51, 127.23, 127.15, 126.64, 126.15, 115.87, 115.79, 115.60, 115.51, 58.65, 57.40, 56.61, 56.43, 50.61, 50.09, 42.76, 41.96, 41.55, 39.84, 38.39, 37.77, 36.89, 34.65, 34.09, 26.59, 23.26, 23.07, 7.20, 7.12, 4.83, 4.69, 4.45; MS, (ES-MS) m/z 573 (M+1).

後処理

  1. extractionextracted with water
  2. dry with materialbrine, dried
  3. concentrationconcentrated in vacuo
  4. customto afford a residue which
  5. customis purified over silica gel

出典と根拠

ORDレコード
ord-da85c5939c2a487cb2b669773f7f0905
出典データセット
uspto-grants-2006_11
特許番号
US07132539B2

反応ノート

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