Hydrochloric Acid → HCID 178451201, compound

HRID 2272636Notes

Reaction equation

HRID 2272636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]([CH2:25][C@@H:26]([OH:30])[C:27]([OH:29])=[O:28])[NH:16][C:17]([C:19]3[O:23][N:22]=[C:21]([OH:24])[CH:20]=3)=[O:18])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:31](O)[CH2:32][CH3:33].Cl.O1CCOC[CH2:37]1>>[CH2:33]([O:28][C:27](=[O:29])[C@H:26]([OH:30])[CH2:25][N:15]([CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:13][CH:12]=1)[NH:16][C:17]([C:19]1[O:23][N:22]=[C:21]([OH:24])[CH:20]=1)=[O:18])[CH2:32][CH2:31][CH3:37]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 312751,4-DioxaneHCID 178523953HCID 178523953, compound

Product 1

HCID 178451201HCID 178451201, compoundYield 88.1%

Procedure

(R)-3-[N-(3′-Chlorobiphenyl-4-ylmethyl)-N′-(3-hydroxy-isoxazole-5-carbonyl)-hydrazino]-2-hydroxy-propionic acid (60 mg, 0.1 mmol) was dissolved in 1-propanol (4 mL, 50 mmol) and 4 M HCl in dioxane (700 mL, 3 mmol) was added. The mixture was stirred at room temperature until the reaction was complete (˜3 hours), then evaporated under reduced pressure and purified (Interchim reverse phase chromatography column, 30-95% MeCN in water with 5% TFA). The clean fractions were combined and lyophilized, then purified by preparative HPLC to yield the title compound (43 mg, purity 95%). MS m/z [M+H]+ calc'd for C24H26ClN3O6, 488.15. found 488.4.

Workup

  1. custom(˜3 hours)
  2. customevaporated under reduced pressure
  3. custompurified (Interchim reverse phase chromatography column, 30-95% MeCN in water with 5% TFA)
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-2da94022cebd48e78e09fa93400a6fc2
Source dataset
uspto-grants-2015_09
Patent number
US09120758B2

Reaction notes

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