Hydrochloric Acid → HCID 178445075, compound

HRID 2275489Notes

Reaction equation

[C:1]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:23][C:24]([C:26]2[N:27]=[N:28][NH:29][CH:30]=2)=[O:25])[CH2:9][C@@:10]([CH3:22])([CH2:14][O:15]C2CCCCO2)[C:11](O)=[O:12])=[CH:3][CH:2]=1.[CH2:37]([OH:43])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].Cl.O1CCOCC1>>[CH2:37]([O:43][C:11](=[O:12])[C@@:10]([CH2:14][OH:15])([CH3:22])[CH2:9][C@H:8]([NH:23][C:24]([C:26]1[N:27]=[N:28][NH:29][CH:30]=1)=[O:25])[CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:6][CH:5]=1)[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 81031-Hexanol

HCID 312751,4-Dioxane

HCID 178458454HCID 178458454, compound

Product 1

HCID 178445075HCID 178445075, compoundYield 51.8%

Conditions

Temperature: 60 °C

Procedure

(2S,4R)-5-Biphenyl-4-yl-2-methyl-2-(tetrahydropyran-2-yloxymethyl)-4-[(1H-1,2,3-triazole-4-carbonyl)amino]pentanoic acid (100 mg, 0.2 mmol) was combined with 1-hexanol (0.3 mL, 2 mmol) and 4 M HCl in 1,4-dioxane (0.3 mL, 1 mmol). The mixture was stirred for 2 hours at 60° C. The mixture was concentrated under reduced pressure and the residue was purified by reverse phase chromatography to yield the title compound (51 mg). MS m/z [M+H]+ calc'd for C28H36N4O4, 493.27. found 493.

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-88e84174ffaf4fb7b838bf5e2e8f9400
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126956B2

Reaction notes

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