Iodoacetic Acid → HCID 11006035、化合物

HRID 225518

反応式

HRID 225518 の反応式
C1CCC(N=C=NC2CCCCC2)CC1.[I:16][CH2:17][C:18]([OH:20])=[O:19].[CH:21]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[C:32][C:33]2[CH:38]=[C:37]([O:39][CH3:40])[C:36]([O:41][CH:42]([CH3:44])[CH3:43])=[CH:35][C:34]=2O)=[CH:27][C:26]=1[O:46][CH3:47])([CH3:23])[CH3:22]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[I:16][CH2:17][C:18]([O:20][C:29]1[CH:30]=[C:25]([O:24][CH:21]([CH3:22])[CH3:23])[C:26]([O:46][CH3:47])=[CH:27][C:28]=1[C:31]#[C:32][C:33]1[CH:34]=[CH:35][C:36]([O:41][CH:42]([CH3:44])[CH3:43])=[C:37]([O:39][CH3:40])[CH:38]=1)=[O:19]

参加物

6

反応物 3

HCID 5240Iodoacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 21923143HCID 21923143、化合物

生成物 1

HCID 11006035HCID 11006035、化合物収率 97%

試薬・触媒・溶媒 2

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

反応条件

温度
18 °C

実験手順

DCC (1.60 g, 7.75 mmol) was added to a solution of 2-iodoacetic acid (1.44 g, 7.74 mmol), 2-[(4-isopropoxy-3-methoxy-phenyl)ethynyl]-5-isopropoxy-4-methoxyphenol (2.6 g, 7.03 mmol)and DMAP (43 mg, 0.35 mmol) in CH2Cl2 (30 mL) and the solution thereby obtained was stirred at 18° C. for 3 h. The resulting suspension was filtered (CH2Cl2 rinse) and the filtrate concentrated under reduced pressure. The residue was suspended in ether (30 mL) at 0° C. with rapid stirring then filtered [rinsing with Et2O (20 mL) pre-cooled at 0° C.] giving the title compound (3.67 g, 97%) as a cream solid mp 127-8° C. IR (KBr disc, cm−1) 2969, 2930, 2833, 1755, 1611, 1575, 1516, 1467, 1416, 1402, 1385, 1365, 1320, 1252, 1236, 1212, 1135, 1108. 1H NMR (300 MHz, CDCl3) δ 7.08 (dd, J=1.8, 8.4 Hz, 1H), 7.04 (d, J=2.1 Hz, 1H), 7.01 (s, 1H), 6.82 (d, J=8.4 Hz, 1H), 6.65 (s, 1H), 4.53 (septet, J=6.0 Hz, 2 Hz), 3.95 (s, 2H), 3.85 (s, 6H), 1.38 (d, J=6.0 Hz, 6H), 1.37 (d, J=6.0 Hz, 6H). 13C NMR+APT (75.5 MHz, CDCl3) δ 167.3 (C), 150.0 (C), 148.4 (C), 148.3 (C), 148.2 (C), 145.1 (C), 125.2 (CH), 115.6 (C), 115.3 (CH), 115.2 (CH), 115.0 (CH), 108.8 (CH), 93.6 (C), 82.7 (C), 72.0 (CH), 71.6 (CH), 56.5 (CH3), 56.3 (CH3), 22.3 (CH3), 22.0 (CH3), −6.2 (CH2). MS (70 eV) m/z (%): 538 (80, M+·), 496 (10, M+·-CH2CHCH3), 370 (10, M+·-CH2ICO), 328 (34), 286 (100); HRMS calcd for C24H27O6I 538.0852. Found 538.0854.

後処理

  1. customthe solution thereby obtained
  2. filtrationThe resulting suspension was filtered
  3. wash(CH2Cl2 rinse)
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customwas suspended in ether (30 mL) at 0° C.
  6. stirringwith rapid stirring
  7. filtrationthen filtered
  8. wash[rinsing with Et2O (20 mL) pre-cooled at 0° C.]

出典と根拠

ORDレコード
ord-ab9cd7a1a13f46d6af933c89d636ea68
出典データセット
uspto-grants-2009_07
特許番号
US07557118B2

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