tert-Butanol → HCID 59607675、化合物

HRID 70884ノート

反応式

HRID 70884 の反応式
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1.[CH3:27][C:28](O)([CH3:30])[CH3:29].CCN=C=NCCCN(C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:2]=[CH:3][C:4]([CH2:7][CH:8]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:9][C:10]([O:12][C:28]([CH3:30])([CH3:29])[CH3:27])=[O:11])=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 6386tert-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 36392483-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(4-phenylphenyl)butanoic Acid

生成物 1

HCID 59607675HCID 59607675、化合物収率 38%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)butanoic acid (250 mg, 0.703 mmol), tBuOH (0.135 ml, 1.407 mmol), EDCI (270 mg, 1.407 mmol) and 4-dimethylaminopyridine (86.0 mg, 0.704 mmol) in DCM (7 ml) is allowed to stir at room temperature under nitrogen for 62 hours. The reaction is quenched with water, and the organic layer is separated and concentrated. The residue is purified by flash column chromatography on silica gel to give tert-butyl 4-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)butanoate (110 mg); HPLC retention time=1.77 minutes (condition B); MS (ES+)=412.1 (m+1) 300.0 (m-tBux2+3; 100%); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.41 (s, 9 H) 1.47 (s, 9 H) 2.36 (A of ABX, Jab=15.5 Hz, Jax=6.2 Hz, 1 H) 2.44 (B of ABX, Jab=15.5 Hz, Jbx=5.6 Hz) 2.82-2.94 (m, 2 H) 4.11-4.17 (m, 1 H) 5.08-5.10 (m, 1 H) 7.25-7.34 (m, 3H) 7.41-7.44 (m, 2 H) 7.51-7.58 (m, 4 H).

後処理

  1. customThe reaction is quenched with water
  2. customthe organic layer is separated
  3. concentrationconcentrated
  4. customThe residue is purified by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-b49c884563ee4a9999d11fbd765862dc
出典データセット
uspto-grants-2014_09
特許番号
US08822534B2

反応ノート

読み込み中…