Hydrochloric Acid → HCID 178476259, compound

HRID 2275486Notes

Reaction equation

HRID 2275486 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]2[CH2:21]CCC[O:17]2)[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.Cl.O1CCOCC1.CC#N.C(Cl)Cl.C(Cl)(=O)C.CCN(C(C)C)C(C)C>>[C:16]([O:15][CH2:14][C@:10]([CH3:22])([CH2:9][C@H:8]([NH:23][C:24]([C:26]1[NH:27][N:28]=[N:29][CH:30]=1)=[O:25])[CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:2][CH:3]=1)[C:11]([OH:13])=[O:12])(=[O:17])[CH3:21]

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 178458454HCID 178458454, compound

Product 1

HCID 178476259HCID 178476259, compoundYield 4.4%

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 mL, 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 acetyl chloride (24 mg, 306 μmol) were added, followed by DIPEA (133 mL, 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 C24H26N4O5, 451.19. found 451.

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-1d685819a1c04b34a3da6e43c7651fef
Source dataset
uspto-grants-2015_09
Patent number
US09126956B2

Reaction notes

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