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Aminoisobutyric acid → 2-[(3,5-Bis-benzyloxy-pyridine-2-carbonyl)-amino]-2-methylpropionic acid methyl ester

HRID 1158572
ノート
印刷プレビュー

反応式

HRID 1158572 の反応式
[CH2:1]([O:8][C:9]1[C:10]([C:23](O)=[O:24])=[N:11][CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26]N(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:47][C:48]([CH3:53])([CH3:52])[C:49]([OH:51])=[O:50]>CN(C=O)C>[CH3:26][O:50][C:49](=[O:51])[C:48]([NH:47][C:23]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][N:11]=1)=[O:24])([CH3:53])[CH3:52]
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 6119Aminoisobutyric acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 534879953,5-Bis(benzyloxy)picolinic acid

生成物 1

HCID 595130922-[(3,5-Bis-benzyloxy-pyridine-2-carbonyl)-amino]-2-methylpropionic acid methyl ester収率 45%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a solution of 3,5-bis-benzyloxy-pyridine-2-carboxylic acid, 2, (1.0 g, 2.99 mmol) in DMF (20 mL) at room temperature under N2 is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) (0.925 g, 5.97 mmol) and 1-hydroxybenzotriazole (HOBt) (0.806 g, 5.97 mmol). The mixture is stirred for 15 minutes after which α-aminoisobutyric acid (0.917 g, 5.97 mmol) and diisopropylethyl-amine amine (DIPEA) (1.56 mL, 8.96 mmol) are added. The resulting solution is stirred at room temperature for 16 hours then concentrated under reduced pressure. The resulting brown oil is purified over silica (EtOAc:heptane 1:1) to afford 0.58 g (45% yield) of the desired compound as a colorless solid. 1H NMR (250 MHz, CDCl3) δ ppm 8.13 (1H, s), 8.02 (1 H, d, J=2.3 Hz), 7.31-7.48 (10H, m), 6.90 (1H, d, J=2.3 Hz), 5.19 (2H, s), 5.10 (2H, s), 3.74 (3H, s), 1.58 (6H, s). HPLC-MS: m/z 435 [M+H]+.

後処理

  1. additionare added
  2. concentrationthen concentrated under reduced pressure
  3. customThe resulting brown oil is purified over silica (EtOAc:heptane 1:1)

出典と根拠

ORDレコード
ord-5e928fa8ff314cf0aefab1fafdea9de3
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07811595B2

反応ノート

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