Sodium Iodide → HCID 86705510, compound

HRID 2279513Notes

Reaction equation

HRID 2279513 reaction equation
CS(O[CH2:6][C@@H:7]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=1)(=O)=O.C1COCC1.CC(C)=O.[Na+].[I-:34]>O>[Cl:15][C:10]1[CH:9]=[C:8]([C@H:7]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:6][I:34])[CH:13]=[CH:12][C:11]=1[F:14]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 22559816Acetone tetrahydrofuranHCID 86705508HCID 86705508, compound

Product 1

HCID 86705510HCID 86705510, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 224 (1.5 g, 4.1 mmol) and THF/acetone (24 mL, 5:1) was added NaI (3.1 g, 20 mmol) and the reaction was stirred at RT overnight. The reaction mixture was poured into water and extracted with EtOAc. The combined organic fractions were dried (MgSO4), filtered, and concentrated in vacuo to afford 1.6 g (98%) of (S)-tert-butyl 1-(3-chloro-4-fluorophenyl)-2-iodoethylcarbamate which was used without additional purification.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d4db1ca2deb4efbb9578add096249ef
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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