Toluene → (2S)-2-[(1H-imidazole-2-carbonyl)-amino]-propionic acid

HRID 491969Notes

Reaction equation

HRID 491969 reaction equation
C([O:5][C:6](=[O:17])[C@@H:7]([NH:9][C:10]([C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)=[O:11])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[NH:13]1[CH:14]=[CH:15][N:16]=[C:12]1[C:10]([NH:9][C@@H:7]([CH3:8])[C:6]([OH:17])=[O:5])=[O:11]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57462011HCID 57462011, compound

Product 1

HCID 57462012(2S)-2-[(1H-imidazole-2-carbonyl)-amino]-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (2S)-2-[(1H-imidazole-2-carbonyl)-amino]-propionic acid tert-butyl ester (0.257 g) in dichloromethane (2 ml) was cooled to 0° C. before dropwise addition of trifluoroacetic acid and the reaction mixture was warmed to room temperature and stirred for 2 hr before evaporation under reduced pressure. The residue was co-evaporated with dichloromethane (twice) and toluene (twice) to leave the required (2S)-2-[(1H-imidazole-2-carbonyl)-amino]-propionic acid that was used without further purification (0.40 g).

Sources & evidence

ORD record
ord-87315f9b855b40febf731ecc48229264
Source dataset
uspto-grants-2009_05
Patent number
US07531570B2

Reaction notes

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