Sodium Carbonate → HCID 67645316, compound

HRID 355326Notes

Reaction equation

HRID 355326 reaction equation
[N+](C1C=CC(CO[C:12](=O)[CH2:13][C:14](=[O:35])[CH2:15][C@:16]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([NH2:27])[C:17]([O:19]CC2C=CC=CC=2)=[O:18])=CC=1)([O-])=O.C([O-])([O-])=O.[Na+].[Na+].I[CH2:44][CH2:45][CH2:46][CH2:47]I>CN(C=O)C>[C:28]([C@:16]([NH2:27])([CH2:15][C:14](=[O:35])[CH2:13][CH:12]1[CH2:47][CH2:46][CH2:45][CH2:44]1)[C:17]([OH:19])=[O:18])([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123371,4-DiiodobutaneHCID 86748376HCID 86748376, compound

Product 1

HCID 67645316HCID 67645316, compoundYield 149.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-2(S)-amino-4-keto-1,6-hexanedioic acid 1-benzyl ester 6-(4-nitrophenyl)methyl ester (4.8 g, 9.6 mmol) was dissolved in DMF (100 mL). Na2CO3 (4.07 g, 38.4 mmol) and 1,4-diiodobutane (3.59 g, 11.6 mmol) were added to the solution. The mixture was stirred 18 h at room temperature and then heated at 50° for 3 h. Evaporation of the solvent, dissolution of the resulting residue with EtOAc, washing of the resulting solution with 1N aqueous HCl and water, followed by drying (MgSO4) and evaporation gave a crude product. The crude product was purified by chromatography {SiO2, eluent: hexane-EtOAc (4:1)} to give the corresponding benzyl ester of the title compound (4.3 g). The benzyl ester was subjected to hydrogenolysis {20% Pd(OH2)/C in MeOH, 18 h} and worked up (see section (d) of example 8 hereinafter) to give the title compound (140 mg). NMR and mass spectrum of the product were in agreement with the expected structure.

Workup

  1. temperatureheated at 50° for 3 h
  2. customEvaporation of the solvent, dissolution of the resulting residue with EtOAc
  3. washwashing of the resulting solution with 1N aqueous HCl and water
  4. customby drying
  5. custom(MgSO4) and evaporation
  6. customgave a crude product
  7. customThe crude product was purified by chromatography {SiO2, eluent

Sources & evidence

ORD record
ord-ba2a5fb487664ab59b3c762ab35eb48d
Source dataset
uspto-grants-1998_11
Patent number
US05830864

Reaction notes

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