Hydrochloric Acid → HCID 178459596, compound

HRID 1043982Notes

Reaction equation

HRID 1043982 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C@H:5]([OH:31])[CH2:6][N:7]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)=[CH:20][CH:19]=1)[NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([OH:16])[CH:12]=1)=[O:10])[CH3:2].[CH:33](O)(C)C.Cl.O1CCOCC1>>[CH:1]([O:3][C:4](=[O:32])[C@H:5]([OH:31])[CH2:6][N:7]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)=[CH:20][CH:19]=1)[NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([OH:16])[CH:12]=1)=[O:10])([CH3:33])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 312751,4-DioxaneHCID 178472580HCID 178472580, compound

Product 1

HCID 178459596HCID 178459596, compoundYield 7.7%

Procedure

(R)-3-[N-(3′-Chlorobiphenyl-4-ylmethyl)-N′-(3-hydroxy-isoxazole-5-carbonyl)-hydrazino]-2-hydroxy-propionic acid ethyl ester (1.4 g, 3.0 mmol) was dissolved in isopropyl alcohol (20 mL, 0.2 mol) and 4 M HCl in dioxane (9 mL, 40 mmol) was added. The mixture was stirred at room temperature overnight (18 hours). The mixture was warmed to 60° C. for 1 hour, then cooled back to room temperature and stirred for 2 hours. The mixture was concentrated and purified (Interchim C18 reverse phase chromatography column, 30-90% MeCN in water for 22 minutes). The clean fractions were combined and lyophilized to yield the title compound (110 mg; purity 98%). MS m/z [M+H]+ calc'd for C23H24ClN3O6, 474.14. found 474.2.

Workup

  1. temperatureThe mixture was warmed to 60° C. for 1 hour
  2. temperaturecooled back to room temperature
  3. stirringstirred for 2 hours
  4. concentrationThe mixture was concentrated
  5. custompurified (Interchim C18 reverse phase chromatography column, 30-90% MeCN in water for 22 minutes)

Sources & evidence

ORD record
ord-5b7018983290405c95f632930fc12259
Source dataset
uspto-grants-2013_10
Patent number
US08563512B2

Reaction notes

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