Sodium Iodide → HCID 10648076, compound

HRID 1923994Notes

Reaction equation

HRID 1923994 reaction equation
CS(O[CH2:6][C@H:7]([NH:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]([O:10][CH3:11])=[O:9])(=O)=O.[I-:32].[Na+]>CC(C)=O>[I:32][CH2:6][C@H:7]([NH:12][C:13]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 13964106HCID 13964106, compound

Product 1

HCID 10648076HCID 10648076, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl (2S)-3-[(methylsulfonyl)oxy]-2-(tritylamino)propanoate CII (22 g; 0.05 mol) in acetone (700 mL) was added sodium iodide (150 g; 1.0 mol) and stirred at r.t. for one week under argon. The acetone was evaporated and the residue was dissolved in diethyl ether (1.5 L). The solids were filtered and the solvent reduced to 1 L before washing with 10% aq Na2S2O3 (3×) and water (200 mL). The solvent was removed under reduced pressure and the residue purified on a silica gel column (10:1→2:1 hexane/EtOAc) and then crystallized from hexane. The methyl (2R)-3-iodo-2-(tritylamino)propanoate CIII was obtained as yellow foam (21 g; 0.045 mol; 89% yield). 1H NMR (CDCl3) [2.25-2.28 (m, 1st rotamer), 2.89 (d, J=10 Hz, 2nd rotamer), 1H], [2.54 (dd, J=13 Hz, J=6 Hz), 3.21 (dd, J=10 Hz, J=8 Hz), 1st rotamer, 1H], [2.69 (dd, J=12 Hz, J=8 Hz), 3.35 (dd, J=10 Hz, J=3 Hz), 2nd rotamer, 1H], [3.31 (s, 1st rotamer), 3.77 (s, 2nd rotamer), 3H], [3.48 (ddd, J=10 Hz, J=7 Hz, J=3 Hz, 2nd rotamer), 4.39 (dd, J=8 Hz, J=6 Hz, 1st rotamer), 1H], 7.18-7.22 (m, 3H), 7.29 (dd, J=8 Hz, J=7 Hz, 6H), [7.45 (d, J=8 Hz, 1st rotamer), 7.50 (d, J=8 Hz, 2nd rotamer), 6H].

Workup

  1. customThe acetone was evaporated
  2. dissolutionthe residue was dissolved in diethyl ether (1.5 L)
  3. filtrationThe solids were filtered
  4. washbefore washing with 10% aq Na2S2O3 (3×) and water (200 mL)
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified on a silica gel column (10:1→2:1 hexane/EtOAc)
  7. customcrystallized from hexane

Sources & evidence

ORD record
ord-8351dcd294bf416c8f4eadc432f3d425
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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