244205-60-5 → 1-Amino-2-phenylcyclopropane-1-carboxylic acid

HRID 898860Notes

Reaction equation

HRID 898860 reaction equation
C(OC([NH:8][C@:9]1([C:18]([OH:20])=[O:19])[CH2:11][C@H:10]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)(C)(C)C.Cl.O1CCOCC1>C(OCC)C>[NH2:8][C@@:9]1([C:18]([OH:20])=[O:19])[CH2:11][C@@H:10]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2734148244205-60-5HCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 1338301-Amino-2-phenylcyclopropane-1-carboxylic acidYield 101.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To commercially available (1R,2S)-1-tert-butoxycarbonylamino-2-phenylcyclopropanecarboxylic acid (130 mg, 0.45 mmol) was added 4N hydrochloric acid—1,4-dioxane solution (2.0 mL, 16 v/w) and the mixture was stirred for 1 hr at room temperature. Diethyl ether (1.0 mL) was added thereto and the mixture was stirred for 5 min, after which the resulting crystals were collected by filtration. The crystals were washed with diethyl ether (1.0 mL) and dried under reduced pressure to give the title compound (81 mg, white powder, yield 84%).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. filtrationafter which the resulting crystals were collected by filtration
  3. washThe crystals were washed with diethyl ether (1.0 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-afd4e59a7c8a428b82db1d71553f88a6
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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