Diisopropylethylamine → (4-{4-[(1H-Imidazol-2-yl-carbamoyl)methoxy]phenyl}butyl)carbamic acid tert-butyl ester

HRID 132568

反応式

HRID 132568 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:23]=[CH:22][C:16]([O:17][CH2:18][C:19]([OH:21])=O)=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=NC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.Cl.S(O)(O)(=O)=O.[NH2:60][C:61]1[NH:62][CH:63]=[CH:64][N:65]=1>C1COCC1.CN(C1C=CN=CC=1)C.CC#N.C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19](=[O:21])[NH:60][C:61]2[NH:62][CH:63]=[CH:64][N:65]=2)=[CH:22][CH:23]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

10

反応物 5

HCID 81531DiisopropylethylamineHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22054428[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acid

生成物 1

HCID 21031134(4-{4-[(1H-Imidazol-2-yl-carbamoyl)methoxy]phenyl}butyl)carbamic acid tert-butyl ester収率 66.5%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acid 33 (1.19 g, 3.68 mmol) was dissolved in anhydrous THF (10 mL), CH2Cl2 (10 mL) and CH3CN (5 mL). To the solution were sequentially added HOAt (200 mg, 1.47 mmol), DMAP (135 mg, 1.10 mmol), and diisopropylethylamine (3.2 mL, 18.40 mmol), followed by the addition of EDC-HCl (1.03 g, 5.35 mmol). The reaction mixture was stirred at room temperature for 15 min. Amino imidazole sulfate (583 mg, 4.41 mmol) was then added and stirring was continued for 48 h. Solvents were removed by rotary evaporation. The residue was taken up in CH2Cl2 (250 mL), washed with water and brine, and concentrated under reduced pressure. Flash silica gel column chromatography eluting with methanol/dichloromethane (1:30, 1:20, v/v) gave the desired amide as a white solid (0.95 g, 66% yield). 1H NMR (300 MHz, CD3OD) δ 1.40 (s, 9H), 1.42-1.70 (m, 4H), 2.48-2.60 (m, 2H), 3.00-3.20 (m, 2H), 4.65 (s, 2H), 6.79-6.89 (m, 4H), 7.10 (d, 2H). m/z (ESI): 389 [C20H28N4O4+H]+.

後処理

  1. stirringstirring
  2. waitwas continued for 48 h
  3. customSolvents were removed by rotary evaporation
  4. washwashed with water and brine
  5. concentrationconcentrated under reduced pressure
  6. washFlash silica gel column chromatography eluting with methanol/dichloromethane (1:30, 1:20, v/v)

出典と根拠

ORDレコード
ord-8ac4c7d1aa93444b975ad1b799afc8eb
出典データセット
uspto-grants-2008_06
特許番号
US07388013B2

関連ノート

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