Methanesulfonic Acid → (1R,2S)-1-Amino-2-vinylcyclopropanecarboxylic Acid

HRID 623351Notes

Reaction equation

HRID 623351 reaction equation
CS(O)(=O)=O.C(OC([NH:13][C@:14]1([C:19]([OH:21])=[O:20])[CH2:16][C@H:15]1[CH:17]=[CH2:18])=O)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[NH2:13][C@:14]1([C:19]([OH:21])=[O:20])[CH2:16][C@H:15]1[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 10376443(1R,2S)-1-(((1,1-Dimethylethoxy)carbonyl)amino)-2-ethenylcyclopropanecarboxylic acid

Product 1

HCID 10261098(1R,2S)-1-Amino-2-vinylcyclopropanecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Methanesulfonic acid (576 mg, 6 mmol) was added to a solution of (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinyl-cyclopropanecarboxylic acid (1135 mg, 5 mmol) and methylene chloride (5 mL), and the mixture was stirred at 25° C. for 3 hours. When triethylamine (708 mg, 7 mmol) was added thereto, a solid was precipitated. The solid was sufficiently precipitated, and then the solution was stirred at 25° C. for 30 minutes. Thereafter, the solid was separated by filtration under reduced pressure. The solid was washed with methylene chloride (5 mL), and then was subjected to vacuum drying. Thereby, the titled compound was produced as a white solid (665 mg, yield of 100%).

Workup

  1. customa solid was precipitated
  2. customThe solid was sufficiently precipitated
  3. stirringthe solution was stirred at 25° C. for 30 minutes
  4. customThereafter, the solid was separated by filtration under reduced pressure
  5. washThe solid was washed with methylene chloride (5 mL)
  6. customdrying

Sources & evidence

ORD record
ord-9f37ed79177d468bb1f871f948e20772
Source dataset
uspto-grants-2016_04
Patent number
US09302980B2

Reaction notes

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