Hydrochloric Acid → HCID 178454694, compound

HRID 2275487Notes

Reaction equation

HRID 2275487 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][CH:16]2CCCC[O:17]2)[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.Cl.O1CCOCC1.CC#N.C(Cl)Cl.[C:50](Cl)(=O)[CH:51](C)[CH3:52].CCN(C(C)C)C(C)C>>[C:1]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@@H:8]([NH:23][C:24]([C:26]2[NH:27][N:28]=[N:29][CH:30]=2)=[O:25])[CH2:9][C@:10]([CH2:14][O:15][C:16](=[O:17])[CH:51]([CH3:52])[CH3:50])([CH3:22])[C:11]([OH:13])=[O:12])=[CH:5][CH:6]=1

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 178458454HCID 178458454, compound

Product 1

HCID 178454694HCID 178454694, compoundYield 4.1%

Procedure

(2S,4R)-5-Biphenyl-4-yl-2-methyl-2-(tetrahydropyran-2-yloxymethyl)-4-[(1H-1,2,3-triazole-4-carbonyl)amino]pentanoic acid (126 mg, 255 μmol) was combined with 4 M HCl in dioxane (191 μL, 765 μmol) in MeCN (0.7 mL, 10 mmol). The mixture was then concentrated under reduced pressure and the residue was purified by reverse phase chromatography. DCM (1 mL, 20 mmol) and isobutyryl chloride (32.6 mg, 306 μmol) were added, followed by DIPEA (133 μL, 765 μmol). The resulting mixture was stirred for 10 minutes. The solvent was evaporated and the residue was dissolved in AcOH and purified by preparative HPLC to yield the title compound (5 mg). MS m/z [M+H]+ calc'd for C26H30N4O5, 479.22. found 479.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customthe residue was purified by reverse phase chromatography
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in AcOH
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-878f35a4d4644884bcac5b2ca8b2f775
Source dataset
uspto-grants-2015_09
Patent number
US09126956B2

Reaction notes

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