Hydrochloric Acid → HCID 178444142, compound

HRID 2275490Notes

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:44])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].Cl.O1CCOCC1>>[CH2:37]([O:44][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:5]=[CH:6][C:1]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:2][CH:3]=1)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 8129Heptanol

HCID 312751,4-Dioxane

HCID 178458454HCID 178458454, compound

Product 1

HCID 178444142HCID 178444142, compoundYield 59.2%

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-heptanol (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 (60 mg). MS m/z [M+H]+ calc'd for C29H38N4O4, 507.29. found 507.

Workup

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

Sources & evidence

ORD record: ord-87ddb0d7073c4f42b817c13076fc6633
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126956B2

Reaction notes

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