Trifluoroacetic acid → HCID 178484701, compound

HRID 58328Notes

Reaction equation

C(OC([NH:8]/[C:9](=[N:38]\C(OC(C)(C)C)=O)/[N:10]([CH3:37])[CH2:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][P+:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:13])=O)(C)(C)C.[Br-].[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50]>>[F:47][C:48]([F:53])([F:52])[C:49]([O-:51])=[O:50].[F:47][C:48]([F:53])([F:52])[C:49]([O-:51])=[O:50].[NH3+:38][C:9](=[NH:8])[N:10]([CH3:37])[CH2:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][P+:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:13]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178484700HCID 178484700, compound

Product 1

HCID 178484701HCID 178484701, compoundYield 31%

Procedure

N2—{(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide (290 mg, 0.41 mmol) was dissolved in trifluoroacetic acid (1 ml, 10 mmol). After 20 minutes at room temperature, the volatiles were removed under vacuum, and the crude was purified with reverse phase preparative HPLC to give the title compound in a 31% yield.

Workup

customthe volatiles were removed under vacuum
customthe crude was purified with reverse phase preparative HPLC

Sources & evidence

ORD record: ord-781ca6147ec248809f64491715ba408e
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434753B2

Reaction notes

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