Hydrochloric Acid → 3-(3-methyl-4-nitrophenyl)methyl-L-histidine dihydrochloride

HRID 1609477Notes

Reaction equation

[ClH:1].C[O:3][C:4](=[O:31])[C@H:5]([CH2:14][C:15]1[N:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([CH3:30])[CH:22]=2)[CH:18]=[N:17][CH:16]=1)[NH:6]C(OC(C)(C)C)=O>>[ClH:1].[ClH:1].[CH3:30][C:23]1[CH:22]=[C:21]([CH2:20][N:19]2[C:15]([CH2:14][C@@H:5]([C:4]([OH:31])=[O:3])[NH2:6])=[CH:16][N:17]=[CH:18]2)[CH:26]=[CH:25][C:24]=1[N+:27]([O-:29])=[O:28]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 14457529114787-83-6

Product 1

HCID 703463963-(3-methyl-4-nitrophenyl)methyl-L-histidine dihydrochlorideYield 92.9%

Conditions

Temperature: 120 °C

Procedure

A 6N hydrochloric acid solution (54.5 ml) was added to 3-(3-methyl-4-nitrophenyl)methyl-N-t-butoxycarbonyl-L-histidine methyl ester (IX-2) (1.3626 g, 0.00326 mol), and the mixture was refluxed under heating on a 120° C. oil bath for 2.5 hours. The resulting solution was cooled and then concentrated to obtain the objective compound (VIII-2) (1.1406 g; yield: 92.9%) as a light-brown oily material.

Workup

temperaturethe mixture was refluxed
temperatureThe resulting solution was cooled
concentrationconcentrated
customto obtain the objective compound (VIII-2) (1.1406 g; yield: 92.9%) as a light-brown oily material

Sources & evidence

ORD record: ord-aa4706258bea4eadabc30fbe7047d502
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05401736

Reaction notes

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