Ethylene Glycol → HCID 86689016, compound

HRID 40516Notes

Reaction equation

HRID 40516 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=1.[C:14]([C:18]1[CH:28]=[CH:27][C:21]([O:22][CH:23]2[CH2:26][NH:25][CH2:24]2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)(C)C.[Cu]I.C(OCC)(=O)C>[C:14]([C:18]1[CH:28]=[CH:27][C:21]([O:22][CH:23]2[CH2:26][N:25]([C:2]3[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=3)[CH2:24]2)=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 534095613-(4-Tert-butylphenoxy)azetidineHCID 66634778N-[(1S)-1-(4-iodophenyl)ethyl]acetamide

Product 1

HCID 86689016HCID 86689016, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere a mixture of 0.28 g (0.97 mmol) (S)—N-[1-(4-iodo-phenyl)-ethyl]-acetamide (III.1), 0.20 g (0.98 mmol) 3-(4-tert-butyl-phenoxy)-azetidine, 0.0093 g (0.049 mmol) CuI, 0.41 g (1.95 mmol) K3PO4 and 0.12 g (1.95 mmol) ethyleneglycol in 1.0 mL isopropanol is stirred for 12 h at 80° C. 100 mL Ethyl acetate are added and the mixture is washed with ammonia solution (5%, 2×). The aq. layer is extracted with ethyl acetate (1×) and the combined organic layers are dried (MgSO4) and concentrated in vacuo. The residue is purified by HPLC (XBridge, MeOH/water (+0.3% NH4OH)) to yield the desired product.

Workup

  1. washthe mixture is washed with ammonia solution (5%, 2×)
  2. extractionThe aq. layer is extracted with ethyl acetate (1×)
  3. dry with materialthe combined organic layers are dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by HPLC (XBridge, MeOH/water (+0.3% NH4OH))

Sources & evidence

ORD record
ord-bd90f25b2453494399af60cbdbec2fea
Source dataset
uspto-grants-2013_09
Patent number
US08530461B2

Reaction notes

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