Iodine → HCID 11348633, compound

HRID 495213Notes

Reaction equation

HRID 495213 reaction equation
[C:1]([O:5][C:6]([C:8]1[NH:12][C:11]([CH:13]=[O:14])=[C:10](C(O)=O)[C:9]=1[CH2:18][CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[I:25]I>C(Cl)Cl.O>[CH2:18]([C:9]1[C:10]([I:25])=[C:11]([CH:13]=[O:14])[NH:12][C:8]=1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:19]

Participants

6

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 86609514HCID 86609514, compound

Product 1

HCID 11348633HCID 11348633, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(tert-butoxycarbonyl)-4-ethyl-2-formyl-1H-pyrrole-3-carboxylic acid (0.548 g, 2.05 mmol) in CH2Cl2 (8.30 mL) was added a solution of NaHCO3 (0.691 g, 8.21 mmol) water (8.2 mL). The mixture was stirred vigorously during the addition of a solution of KI (1.021 g, 6.15 mmol) and I2 (0.570 g, 2.23 mmol) in water (11.15 mL). The resultant mixture was heated to 45° C. for 60 min until the initial red/brown color faded. The reaction was cooled to ambient temperature and quenched with saturated aqueous Na2SO3 (25 ml) prior to separation of the phases. The aqueous layer was extracted with CH2Cl2 (1×30 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The resultant residue was purified by normal phase chromatography (10-30% ethyl acetate/hexanes). Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CD3OD) δ 9.59 (s, 1H); 2.77 (q, J=7.6 Hz, 2H); 1.60 (s, 9H); 1.10 (t, J=7.6 Hz, 3H). HRMS (ES) exact mass calculated for C12H16INNaO3 (M+Na+): 372.0072. Found 372.0067.

Workup

  1. customquenched with saturated aqueous Na2SO3 (25 ml)
  2. customto separation of the phases
  3. extractionThe aqueous layer was extracted with CH2Cl2 (1×30 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant residue was purified by normal phase chromatography (10-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9a23c06c204e46598271cbeef83a76d4
Source dataset
uspto-grants-2009_05
Patent number
US07538231B2

Reaction notes

Loading…