Sodium Iodide → HCID 68818900, compound

HRID 2111941Notes

Reaction equation

HRID 2111941 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:28]([OH:30])=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[I-].[Na+].[C:40]([O:46][CH2:47]Cl)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]>C(Cl)(Cl)Cl.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[C:40]([O:46][CH2:47][O:29][C:28](=[O:30])[CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])=[CH:16][CH:15]=1)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 15600475HCID 15600475, compound

Product 1

HCID 68818900HCID 68818900, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 2.5 mmol of the compound of Step A above in 15 ml of chloroform there are added (nBu)4NHSO4 (0.5 of an equivalent), triethylamine (2 equivalents), sodium iodide (1 equivalent) and chloromethyl pivalate (2 equivalents). The reaction mixture is refluxed for 18 hours and then concentrated. The residue is dissolved in diethyl ether and is extracted with water, twice with 0.5M HCl, twice with 5% NaHCO3, and with water. The organic phase is concentrated and chromatography (dichloromethane/methanol: 9.9/0.1 to 9.5/0.5) allows the expected product to be isolated.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in diethyl ether
  4. extractionis extracted with water, twice with 0.5M HCl, twice with 5% NaHCO3
  5. concentrationThe organic phase is concentrated
  6. customto be isolated

Sources & evidence

ORD record
ord-6d085cc022244c2d8164c3d2d5bc1a3c
Source dataset
uspto-grants-2009_04
Patent number
US07521469B2

Reaction notes

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