Carbon Dioxide → 6-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

HRID 1587591Notes

Reaction equation

HRID 1587591 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[Na].[CH2:11]([O:18][C:19](Cl)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)=O>O1CCCC1>[C:12]1([CH2:11][O:18][C:19]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 5646-Aminohexanoic AcidHCID 10387Benzyl chloroformateHCID 5360545Sodium

Product 1

HCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-aminocaproic acid (15 g, 0.114 mole) in a 5% aqueous solution of sodium hydroge carbonate (500 ml) and tetrahydrofuran (100 ml), was added benzylchloroformate (19.52 ml, 0.137 mole) dropwise over a 10 minute period. The reaction was allowed to stir at room temperature until carbon dioxide had ceased to eliminate (~24 hours). The reaction was concentrated in vacuo to remove tetrahydrofuran and the aqueous layer was extracted with ethyl acetate and concentrated again to remove organic residue and then acidified to pH 3 and extracted with ethyl acetate (4×), dried over anhydrous magnesium sulfate and concentrated to yield a clear oil. The product was crystallized from ethyl acetate:hexane (1:1). The white solid was recrystallized twice to yield 22.5 g of the title A compound.

Workup

  1. custom(~24 hours)
  2. concentrationThe reaction was concentrated in vacuo
  3. customto remove tetrahydrofuran
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. concentrationconcentrated again
  6. customto remove organic residue
  7. extractionextracted with ethyl acetate (4×)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customto yield a clear oil
  11. customThe product was crystallized from ethyl acetate:hexane (1:1)
  12. customThe white solid was recrystallized twice
  13. customto yield 22.5 g of the title A compound

Sources & evidence

ORD record
ord-6291c7cd396346cfb4a263fc18fda859
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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