Iodine → HCID 66928527, compound

HRID 2065013Notes

Reaction equation

HRID 2065013 reaction equation
N#N.[CH3:3][O:4][C:5](=[O:27])[CH:6]([NH:15][C:16](=[O:26])[CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:7](O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.CCN(CC)CC>C(Cl)Cl>[CH3:3][O:4][C:5]([C:6]1[N:15]=[C:16]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[O:26][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:27]

Participants

8

Reactant 6

HCID 807IodineHCID 947NitrogenHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 159087TriacetoxyperiodinaneHCID 23456069HCID 23456069, compound

Product 1

HCID 66928527HCID 66928527, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(2-tert-butoxycarbonylamino-acetylamino)-3-hydroxy-3-phenyl-propionic acid methyl ester (620 mg, 1.76 mmol) in CH2Cl2 (20.0 mL) was treated at 0° C. with Dess-Martin periodinane (923 mg, 2.11 mmol). The resulting mixture was stirred at rt for 1 h and filtered through a short plug of basic alumina (activity I) and sand into a flask containing a freshly prepared solution of triphenylphosphine (946 mg, 3.55 mmol), I2 (902 mg, 3.52 mmol) and Et3N (0.98 ml, 7.04 mmol) in CH2Cl2 (22.0 mL). The filter cake was washed with CH2Cl2. After 15 min, the reaction mixture was transferred to a separatory funnel, treated with sat. aq. Na2S2O3 (150 mL) and extracted with CH2Cl2 (2×150 mL). The organic layer was washed with sat. aq. NaHCO3 (150 mL), filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (50:50 CH2Cl2-MeOH) gave the title compound as a white solid. TLC: rf (50:50 CH2Cl2-MeOH)=0.33. LC-MS-conditions 02: tR=0.99 min, [M+H]+=333.39.

Workup

  1. filtrationfiltered through a short plug of basic alumina (activity I) and sand into a flask
  2. washThe filter cake was washed with CH2Cl2
  3. waitAfter 15 min
  4. customthe reaction mixture was transferred to a separatory funnel
  5. additiontreated with sat. aq. Na2S2O3 (150 mL)
  6. extractionextracted with CH2Cl2 (2×150 mL)
  7. washThe organic layer was washed with sat. aq. NaHCO3 (150 mL)
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure
  10. customPurification of the residue by FC (50:50 CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-effc51d4b4f4494eab70b38fa64b78bd
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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