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Diisopropylcarbodiimide → 4-(2-[4-(4-Methyl-4-(methyldisulphanyl)pentanoyl)piperazin-1-yl]ethoxy)-2,6-bis(hydroxymethyl)pyridine

HRID 446650
ノート
印刷プレビュー

反応式

HRID 446650 の反応式
[CH3:1][C:2]([S:9][S:10][CH3:11])([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=O.C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[N:32]1([CH2:38][CH2:39][O:40][C:41]2[CH:46]=[C:45]([CH2:47][OH:48])[N:44]=[C:43]([CH2:49][OH:50])[CH:42]=2)[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CN(C=O)C>[CH3:8][C:2]([S:9][S:10][CH3:11])([CH3:1])[CH2:3][CH2:4][C:5]([N:35]1[CH2:36][CH2:37][N:32]([CH2:38][CH2:39][O:40][C:41]2[CH:46]=[C:45]([CH2:47][OH:48])[N:44]=[C:43]([CH2:49][OH:50])[CH:42]=2)[CH2:33][CH2:34]1)=[O:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 115646344-Methyl-4-(methyldisulfanyl)pentanoic acidHCID 670322814-[2-(Piperazin-1-yl)ethoxy]-2,6-bis(hydroxymethyl)pyridine

生成物 1

HCID 866712934-(2-[4-(4-Methyl-4-(methyldisulphanyl)pentanoyl)piperazin-1-yl]ethoxy)-2,6-bis(hydroxymethyl)pyridine収率 39.2%

試薬・触媒・溶媒

1
HCID 6228Dimethylformamide溶媒

実験手順

344 μL of TEA and then, after stirring for 10 min, 748 mg of 4-methyl-4-(methyldisulphanyl)pentanoic acid, 417 μl of diisopropylcarbodiimide and 69 mg of 1-hydroxybenzotriazole hydrate are added to 600 mg of 4-[2-(piperazin-1-yl)ethoxy]-2,6-bis(hydroxymethyl)pyridine in solution in 12 ml of DMF. After 15 h at AT, the mixture is concentrated under RP, 15 ml of water are added and extraction is carried out 2× with AcOEt. The combined organic phases are dried over MgSO4 and concentrated under RP, and the residue is purified by flash chromatography on silica (Analogix Super Flash SiO2 SF25-80 g) using a gradient from 2 to 10% of MeOH in DCM. 390 mg of 4-(2-[4-(4-methyl-4-(methyldisulphanyl)pentanoyl)piperazin-1-yl]ethoxy)-2,6-bis(hydroxymethyl)pyridine are thus obtained.

後処理

  1. concentrationthe mixture is concentrated under RP, 15 ml of water
  2. additionare added
  3. extractionextraction
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. concentrationconcentrated under RP
  6. customthe residue is purified by flash chromatography on silica (Analogix Super Flash SiO2 SF25-80 g)

出典と根拠

ORDレコード
ord-3060a534d5e1498a84c488e918232247
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08481042B2

反応ノート

読み込み中…

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