Sodium Iodide → HCID 54283487, compound

HRID 1583822Notes

Reaction equation

HRID 1583822 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@@H:18]([CH2:29]OS(C)(=O)=O)[O:17][C@@H:6]1[S:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2].[I-:35].[Na+]>CN(C=O)C>[C:1]([O:4][C@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@@H:18]([CH2:29][I:35])[O:17][C@@H:6]1[S:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 54015903HCID 54015903, compound

Product 1

HCID 54283487HCID 54283487, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 10 (2.0 g) and sodium iodide (1.0 g) in DMF (15 ml) is heated with stirring for 16 hours at 70° C. (bath temperature). The mixture is evaporated in vacuo to a residue, which is partitioned between chloroform and water. The organic layer is dried and evaporated to a syrup (2.0 g), which is put on a column of silica gel and eluted with CHCl3 --EtOAc (95:5, v/v). The title compound is isolated in 94% yield: m.p. 91°-92° C. (MeOH); [α]D27 +203±0.9° (C 1.06, CHCl3).

Workup

  1. temperatureis heated
  2. customThe mixture is evaporated in vacuo to a residue, which
  3. customis partitioned between chloroform and water
  4. customThe organic layer is dried
  5. customevaporated to a syrup (2.0 g), which
  6. washeluted with CHCl3 --EtOAc (95:5

Sources & evidence

ORD record
ord-86e9b8b18327406c9527479211003863
Source dataset
uspto-grants-1985_11
Patent number
US04554349

Reaction notes

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