Iodoacetic Acid → HCID 11006035, compound

HRID 225518

Reaction equation

HRID 225518 reaction equation
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]

Participants

6

Reactant 3

HCID 5240Iodoacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 21923143HCID 21923143, compound

Product 1

HCID 11006035HCID 11006035, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
18 °C

Procedure

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.

Workup

  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.]

Sources & evidence

ORD record
ord-ab9cd7a1a13f46d6af933c89d636ea68
Source dataset
uspto-grants-2009_07
Patent number
US07557118B2

Linked notes

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