Sodium Carbonate → HCID 21303770, compound

HRID 2371028Notes

Reaction equation

HRID 2371028 reaction equation
[NH2:1][C:2]1([C:5]([O:7][CH3:8])=[O:6])[CH2:4][CH2:3]1.[C:9]([O-])([O-])=O.[Na+].[Na+].[C:15](Cl)([O:17][CH2:18][CH:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16].O1[CH2:38][CH2:37]OCC1>O>[CH:30]1[C:31]2[CH:19]([CH2:18][O:17][C:15]([NH:1][C:2]3([C:5]([O:7][CH3:8])=[O:6])[CH2:4][CH2:3][CH2:38][CH2:37][CH2:9]3)=[O:16])[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]=2[CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 343679-Fluorenylmethyl chloroformateHCID 2735309Methyl 1-aminocyclopropanecarboxylate

Product 1

HCID 21303770HCID 21303770, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 1-aminocyclopropanecarboxylate (5.8 g, 50.4 mmol) and Na2CO3 (8.0 g, 74.6 mmol) in 1,4-dioxane (50 mL) and water (50 mL) at 0° C. was added FmocCl (19.4 g, 75.2 mmol). The resulting mixture was warmed gradually to room temperature. After the amine was consumed completely as indicated by TLC, water (50 mL) was added and the mixture was extracted with DCM (3×60 mL). The DCM extract was washed with brine, and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (15 g, 88%).

Workup

  1. customAfter the amine was consumed completely
  2. additionwas added
  3. extractionthe mixture was extracted with DCM (3×60 mL)
  4. extractionThe DCM extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationAfter filtration and concentration
  8. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ff23944f859b4332bc212e0affcb3855
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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