Sodium Iodide → HCID 131725712, compound

HRID 1796885Notes

Reaction equation

HRID 1796885 reaction equation
[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3][C:4](CCl)=[O:5].[Na+].[I-].O.[SH:18][C:19]1[N:27]=[CH:26][N:25]=[C:24]2[C:20]=1[NH:21][CH:22]=[N:23]2.C([O-])([O-])=[O:29].[Ca+2]>CC(C)=O.CN(C=O)C>[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3][C:4]([OH:5])=[O:29].[CH:22]1[NH:21][C:20]2[C:19]([N:27]=[CH:26][NH:25][C:24]=2[N:23]=1)=[S:18]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10112Calcium CarbonateHCID 104700691HCID 104700691, compoundHCID 178527204HCID 178527204, compound

Product 1

HCID 131725712HCID 131725712, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of (13) (1.0 g, 4.2 mmol) and NaI (0.755 g, 5.04 mmol) in acetone (15 mL) was stirred for 1 hour at room temperature, followed by addition of a solution of (1) (0.595 g, 3.5 mmol) and CaCO3 (1.738 g, 17.4 mmol) in DMF (15 mL). The mixture was stirred at room temperature overnight, followed by filtration. The filtrate was concentrated in vacuo and the residue dissolved in EtOAc (100 mL), washed with water (100 mL), brine (100 mL), and dried over anhydrous MgSO4. The solvent was removed in vacuo and the residue purified by silica gel column chromatography (0 to 5% MeOH in CHCl3, v/v) to give 340 mg (28.6%) of product (14): 13C NMR (CDCl3+CD3OD) δ 28.429 (3×CH3 of Boc), 34.868 (CH2C(═O)O), 36.109 (NHCH2CH2), 61.223 (OCH2S), 81.537 (C(CH3)3), 142.901 (Ar—C), 145.640 (Ar—C), 148.623 (Ar—C), 149.749 (Ar—C), 152.181 (Ar—C), 156.738 (NHC(═O)O), 172.431 (C(═O)O).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationfollowed by filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue dissolved in EtOAc (100 mL)
  5. washwashed with water (100 mL), brine (100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. customThe solvent was removed in vacuo
  8. customthe residue purified by silica gel column chromatography (0 to 5% MeOH in CHCl3, v/v)

Sources & evidence

ORD record
ord-6ed82187c1a6468a8f974a082c8251d6
Source dataset
uspto-grants-2006_04
Patent number
US07033583B2

Reaction notes

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