Trifluoroacetic acid → HCID 178472540, compound

HRID 1018245Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:38])[C@@H:5]([NH:15][C:16]([C:18]1[CH:37]=[CH:36][C:21]2[N:22]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:23]([C:25]3[CH:29]=[CH:28][O:27][CH:26]=3)=[N:24][C:20]=2[CH:19]=1)=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)[CH3:2].C([Sn]([N:52]=[N+:53]=[N-:54])(CCCC)CCCC)CCC.C(O)(C(F)(F)F)=O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:38])[C@@H:5]([NH:15][C:16]([C:18]1[CH:37]=[CH:36][C:21]2[N:22]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:23]([C:25]3[CH:29]=[CH:28][O:27][CH:26]=3)=[N:24][C:20]=2[CH:19]=1)=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:54][N:53]=[N:52][N:14]=2)=[CH:9][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

(S)-3-(4-Cyanophenyl)-2-{[1-(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazol-5-yl)-methanoyl]-amino}-propionic acid ethyl ester from above (0.260 g, 0.51 mmol) and tributyltin azide (4 equiv., 2.0 mmol, 0.650 g) were dissolved in DMSO (2 mL) and the solution stirred at 80° C. for 48 h. The reaction was then quenched with 1 N HCl (10 mL) and stirred for an additional 40 min. The aqueous phase was decanted and the oily residue dissolved in DMSO and purified by reversed-phase HPLC using 0.1% TFA—0.1% TFA in acetonitrile gradients to give after lyophilisation, the TFA salt of the title compound as a white amorphous solid (97 mg).

Workup

customThe reaction was then quenched with 1 N HCl (10 mL)
stirringstirred for an additional 40 min
customThe aqueous phase was decanted
dissolutionthe oily residue dissolved in DMSO
custompurified by reversed-phase
customto give after lyophilisation

Sources & evidence

ORD record: ord-e51c28a2916f4aaeb7c023a8f047ad86
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479508B1

Reaction notes

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