HCID 57219958, compound → HCID 18611974, compound

HRID 568975Notes

Reaction equation

HRID 568975 reaction equation
[F:1][CH:2]([CH2:15][CH2:16][CH:17]([NH:21]C(OC(C)(C)C)=O)[C:18]([OH:20])=[O:19])[CH:3]([NH:7]C(OC(C)(C)C)=O)[C:4]([OH:6])=[O:5]>CCOCC.Cl>[F:1][CH:2]([CH:3]([C:4]([OH:6])=[O:5])[NH2:7])[CH2:15][CH2:16][C@@H:17]([C:18]([OH:20])=[O:19])[NH2:21]

Participants

4

Reactant 1

HCID 57219958HCID 57219958, compound

Product 1

HCID 18611974HCID 18611974, compoundYield 20.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

3-fluoro-2,6-di-tert.-butoxycarbonylaminopimelic acid (940 mg, 2.3 mmoles) is dissolved in ether saturated with HCl gas, and the mixture is stirred overnight. The white crystals are filtered off and dissolved in isopropanol/ethanol. After filtration through a membrane filter (Millipore), propylene oxide (0.6 mL) is added. The precipitate is stirred with isopropanol and filtered off again. Crystallization from water/ethanol/isopropanol gives the pure title compound (100 mg) containing 0.2 moles of HCl.

Workup

  1. filtrationThe white crystals are filtered off
  2. dissolutiondissolved in isopropanol/ethanol
  3. filtrationAfter filtration through a membrane
  4. filtrationfilter (Millipore), propylene oxide (0.6 mL)
  5. additionis added
  6. stirringThe precipitate is stirred with isopropanol
  7. filtrationfiltered off again
  8. customCrystallization from water/ethanol/isopropanol

Sources & evidence

ORD record
ord-88a9cf49f432435a94f77e993548431e
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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