Trifluoroacetic acid → HCID 54012489, compound

HRID 1367689Notes

Reaction equation

C([O:5][C:6](=[O:28])[C@H:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:8][C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O>>[N+:18]([C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]([NH:8][C@H:7]([C:6]([OH:28])=[O:5])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:10])=[CH:17][CH:16]=1)([O-:20])=[O:19]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 11025478HCID 11025478, compound

Product 1

HCID 54012489HCID 54012489, compoundYield 96%

Procedure

In a nitrogen atmosphere, 193 mg (0.5 mmol) of the N-(4-nitrophenoxycarbonyl)phenylalanine t-butyl ester and 5 mL of trifluoroacetic acid were introduced into a round-bottom flask having a capacity of 10 mL. The contents were stirred at room temperature for 1 hour. This reaction mixture was concentrated under reduced pressure with a vacuum pump and then analyzed by NMR spectroscopy using dioxane as an internal reference. As a result, it was found that N-(4-nitrophenoxycarbonyl)phenylalanine had been obtained in a yield of 96%. Furthermore, this reaction mixture was subjected to column isolation to obtain N-(4-nitrophenoxycarbonyl)phenylalanine in an amount of 160 mg (isolation yield, 97%).

Workup

concentrationThis reaction mixture was concentrated under reduced pressure with a vacuum pump
customhad been obtained in a yield of 96%

Sources & evidence

ORD record: ord-78777427964d4f0598fa9d021eeac1c0
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893274B2

Reaction notes

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