N-(9-Fluorenylmethoxycarbonyloxy)succinimide → HCID 54551150, compound

HRID 863617Notes

Reaction equation

HRID 863617 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][Cl:11])[C:3]([OH:5])=[O:4].[C:12](ON1C(=O)CCC1=O)([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13]>O1CCOCC1.C([O-])(O)=O.[Na+]>[CH:27]1[C:28]2[CH:16]([CH2:15][O:14][C:12]([NH:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][Cl:11])[C:3]([OH:5])=[O:4])=[O:13])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]=2[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 88297188HCID 88297188, compound

Product 1

HCID 54551150HCID 54551150, compoundYield 113.8%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

The amine, (S)-2-amino-7-chloroheptanoic acid (-)-pseudoephedrinyl amide (1.8 mmol, 0.59 g) (for reference, Myers, A. G. et al. J. Am. Chem. Soc. 1995, 117, 8488), was dissolved in 7.2 mL of a heterogeneous mixture (1:1 v/v) of dioxane and saturated aqueous NaHCO3. The mixture was degassed under reduced pressure, placed under nitrogen and chilled to 0° C. To the mixture was added Fmoc-OSu (2.2 mmol, 0.73 g) in four equivalent portions over 15 min. Another 1 mL of dioxane was added to improve solubility of the Fmoc-OSu. The mixture was allowed to stir 20 min at 0° C. and 4 h at 20° C. After the mixture was concentrated under reduced pressure, it was extracted into AcOEt (250 mL). The organic layer was washed with saturated aqueous NaHCO3 (3×5 mL), saturated NaCl (3×5 mL) and dried (MgSO4). After the solvent was removed under reduced pressure, the residue obtained was purified by silica gel chromatography (AcOEt/hexanes:40/60%). The protected compound was obtained as a white foam (0.823 g, 83%) after removal of solvents under reduced pressure: [α]D25 -503.7° (c 0.01, CHCl3), Rf 0.25 (AcOEt/hexanes:1/1).

Workup

  1. customThe mixture was degassed under reduced pressure
  2. concentrationAfter the mixture was concentrated under reduced pressure, it
  3. extractionwas extracted into AcOEt (250 mL)
  4. washThe organic layer was washed with saturated aqueous NaHCO3 (3×5 mL), saturated NaCl (3×5 mL)
  5. dry with materialdried (MgSO4)
  6. customAfter the solvent was removed under reduced pressure
  7. customthe residue obtained
  8. customwas purified by silica gel chromatography (AcOEt/hexanes:40/60%)

Sources & evidence

ORD record
ord-4ad562b6dc5047aebc1bea30d2c4c795
Source dataset
uspto-grants-1998_02
Patent number
US05721338

Reaction notes

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