Ethoxalyl chloride → HCID 59696185, compound

HRID 2113198Notes

Reaction equation

HRID 2113198 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:37]=[CH:36][CH:35]=[CH:34][C:8]=2[C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:19]([NH2:33])[CH:18]=2)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].C(N(C(C)C)CC)(C)C.Cl[C:48](=[O:54])[C:49]([O:51][CH2:52][CH3:53])=[O:50]>ClCCl.O>[CH2:52]([O:51][C:49](=[O:50])[C:48]([NH:33][C:19]1[CH:18]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]([CH2:10][C:9]3[C:8]4[CH:34]=[CH:35][CH:36]=[CH:37][C:7]=4[O:6][C:5]=3[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:16][CH:15]=2)[CH:22]=[CH:21][C:20]=1[O:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:54])[CH3:53]

Participants

6

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 81531DiisopropylethylamineHCID 59855503HCID 59855503, compound

Product 1

HCID 59696185HCID 59696185, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4′-(2-butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-ylamine (129 mg, 0.264 mmol) and diisopropylethylamine (0.115 mL, 2.5 equiv., 0.66 mmol) in dichloromethane (5 mL) was treated with a solution of ethyl chlorooxoacetate (44 mg, 1.2 equiv., 0.317 mmol) in dichloromethane (1 mL). After stirring for 2 h, the solution was diluted with water and extracted with dichloromethane (2×15 mL). The combined organic layers were washed with water, sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by prep thin layer chromatography (25% ethyl acetate in heptane) afforded N-[4′-(2-butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-yl]-oxalamic acid ethyl ester (120 mg, 77%).

Workup

  1. extractionextracted with dichloromethane (2×15 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by prep thin layer chromatography (25% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-beb564235fa645d68772a22c38622d7f
Source dataset
uspto-grants-2009_04
Patent number
US07524878B2

Reaction notes

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