Hydrochloric Acid → HCID 178447529, compound

HRID 2275488Notes

Reaction equation

HRID 2275488 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]([OH:13])=[O:12])=[CH:3][CH:2]=1.Cl.O1CCOCC1.CC#N.C(Cl)Cl.[C:50](Cl)(=[O:55])[CH2:51][CH:52]([CH3:54])[CH3:53].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:6]=[CH:5][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]([CH3:22])([CH2:14][O:15][C:50](=[O:55])[CH2:51][CH:52]([CH3:54])[CH3:53])[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 66054Isovaleryl chlorideHCID 81531DiisopropylethylamineHCID 178458454HCID 178458454, compound

Product 1

HCID 178447529HCID 178447529, compoundYield 2.4%

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 isovaleryl chloride (39.9 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 (3 mg). MS m/z [M+H]+ calc'd for C27H32N4O5, 493.24. found 493.

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-6002197dc6844984bc6a08cae07c281c
Source dataset
uspto-grants-2015_09
Patent number
US09126956B2

Reaction notes

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