Sulfuric Acid → rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

HRID 2261714Notes

Reaction equation

HRID 2261714 reaction equation
[CH2:1]([O:3][C:4]([C@@:6]1([NH:11]C(OC(C)(C)C)=O)[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].S(=O)(=O)(O)O.CN(C=O)C>CCOC(C)=O>[CH2:1]([O:3][C:4]([C@@:6]1([NH2:11])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 10658673Ethyl (1R,2S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenylcyclopropanecarboxylate

Product 1

HCID 10820795rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 153.2 g (600 mmol) of (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid ethyl ester (commercially available from Synthetech Oregon, USA) in 80 mL of EtOAc was dosed to a solution of 65.1 g (630 mmol) of sulfuric acid in 480 mL of EtOAc at 20-25° C. The reaction mixture was stirred for 60 min at 42-48° C. After complete conversion the reaction mixture was cooled to 18-22° C. Then 127.5 g (1260 mmol) of TEA was dosed at 20-30° C. Finally 100 mL of DMF was added. The reaction mixture was used in the next step immediately after preparation.

Workup

  1. temperatureAfter complete conversion the reaction mixture was cooled to 18-22° C
  2. customwas dosed at 20-30° C
  3. customimmediately after preparation

Sources & evidence

ORD record
ord-1df713505fcd49969bc81068b4ef53e1
Source dataset
uspto-grants-2010_12
Patent number
US07847106B2

Reaction notes

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