1,4-Dioxane → HCID 69200775, compound

HRID 857810Notes

Reaction equation

HRID 857810 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[O:10][CH:11]=[CH:12][C:13]=1[C@H:14]([CH3:18])[C:15]([OH:17])=[O:16].O1CCOCC1.[C:25](Cl)([O:27][CH2:28][CH:29]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26]>C([O-])([O-])=O.[Na+].[Na+].O>[C:25]([NH:8][C:9]1[O:10][CH:11]=[CH:12][C:13]=1[C@H:14]([CH3:18])[C:15]([OH:17])=[O:16])([O:27][CH2:28][CH:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:36]2[C:41]1=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:26]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 343679-Fluorenylmethyl chloroformateHCID 69433043HCID 69433043, compound

Product 1

HCID 69200775HCID 69200775, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

(S)-2-amino-3-furylpropionic acid trifluroacetic acid salt (0.47 g) was dissolved in 30 mL of 10% Na2CO3 and 5 mL of dioxane and was cooled to 0 C. A solution of FMOC—Cl (0.53 g) in 10 mL was added dropwise. The mixture was then stirred for 15 min. at 0 C. and 2 hr at room temperature. The mixture was diluted with H2O, extracted with diethyl ether, and acidified with citric acid. The mixture was filtered and washed with H2O until neutral. The solid was then dissolved in ethylacetate, dried over Na2SO4, concentrated in vacuo to give the product as a white foam.

Workup

  1. custom2 hr
  2. customat room temperature
  3. extractionextracted with diethyl ether
  4. filtrationThe mixture was filtered
  5. washwashed with H2O until neutral
  6. dissolutionThe solid was then dissolved in ethylacetate
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8918e36623354f128edfb971013410cc
Source dataset
uspto-grants-2006_12
Patent number
US07147858B2

Reaction notes

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