Potassium Iodide → HCID 117598736, compound

HRID 522415Notes

Reaction equation

HRID 522415 reaction equation
FC(F)(F)[C:3]([O-:5])=[O:4].[CH:8]1([C@H:14]2[C:47](=[O:48])[N:46]3[CH2:49][C@@H:43]([CH2:44][C@H:45]3[C:50](=[O:67])[NH:51][C@:52]3([C:57](=[O:66])[NH:58][S:59]([C:62]4([CH3:65])[CH2:64][CH2:63]4)(=[O:61])=[O:60])[CH2:54][C@H:53]3[CH:55]=[CH2:56])[O:42][C:26]3=[N:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=4[C:34]([O:35][CH:36]4[CH2:41][CH2:40][NH2+:39][CH2:38][CH2:37]4)=[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[CH2:68][C@H:18]3[O:17][C:16](=[O:69])[NH:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C.[I-].[K+].Br[CH2:80][CH2:81][O:82][CH3:83]>CN(C=O)C.O>[CH:3]([O-:5])=[O:4].[CH:8]1([C@H:14]2[C:47](=[O:48])[N:46]3[CH2:49][C@@H:43]([CH2:44][C@H:45]3[C:50](=[O:67])[NH:51][C@:52]3([C:57](=[O:66])[NH:58][S:59]([C:62]4([CH3:65])[CH2:63][CH2:64]4)(=[O:61])=[O:60])[CH2:54][C@H:53]3[CH:55]=[CH2:56])[O:42][C:26]3=[N:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=4[C:34]([O:35][CH:36]4[CH2:37][CH2:38][NH+:39]([CH2:80][CH2:81][O:82][CH3:83])[CH2:40][CH2:41]4)=[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[CH2:68][C@H:18]3[O:17][C:16](=[O:69])[NH:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 809722-Bromoethyl methyl etherHCID 117598881HCID 117598881, compound

Product 1

HCID 117598736HCID 117598736, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of the product from Step 1, Example 236 (100 mg, 0.101 mmol) in DMF (3 mL) was added triethylamine (0.070 mL, 0.506 mmol), potassium iodide (3.36 mg, 0.020 mmol) and 2-bromoethylmethylether (42.2 mg, 0.303 mmol). The reaction was heated to 55° C. and stirred for 4 hours at which stage LCMS indicated no starting material. After cooling to room temperature, water was added and the reaction was extracted with ethyl acetate. The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated to give an oily residue, which was purified by HPLC (0 to 90% acetonitrile in water; with 0.1% HCOOH) to furnish the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction was extracted with ethyl acetate
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give an oily residue, which
  7. customwas purified by HPLC (0 to 90% acetonitrile in water; with 0.1% HCOOH)

Sources & evidence

ORD record
ord-be58d531bd824b7a87dadc0f9f5d0cd4
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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