Hydrochloric Acid → HCID 178451200, compound

HRID 2272637Notes

Reaction equation

HRID 2272637 reaction equation
C([O:3][C:4](=O)[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])C.[CH2:33]([OH:37])[CH:34]([CH3:36])[CH3:35].Cl.O1CCOCC1>>[CH2:33]([O:37][C:4](=[O:3])[C@H:5]([OH:31])[CH2:6][N:7]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)=[CH:22][CH:23]=1)[NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([OH:16])[CH:12]=1)=[O:10])[CH:34]([CH3:36])[CH3:35]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6560IsobutanolHCID 312751,4-DioxaneHCID 178472580HCID 178472580, compound

Product 1

HCID 178451200HCID 178451200, compoundYield 58.9%

Procedure

(R)-3-[N-(3′-Chlorobiphenyl-4-ylmethyl)-N′-(3-hydroxy-isoxazole-5-carbonyl)-hydrazino]-2-hydroxy-propionic acid ethyl ester (1.5 g, 3.3 mmol) was dissolved in isobutyl alcohol (20 mL, 200 mmol) and 4 M HCl in dioxane (10 mL, 40 mmol) was added. The mixture was stirred at room temperature for 6 hours. The mixture was concentrated, dissolved in water/MeCN/MeOH, and purified (Interchim C18 reverse phase chromatography column, 25-75% MeCN in water for 22 minutes). The clean fractions were combined and lyophilized to yield the title compound (948 mg; purity 99%). MS m/z [M+H]+ calc'd for C24H26ClN3O6, 488.15. found 488.4.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in water/MeCN/MeOH
  3. custompurified (Interchim C18 reverse phase chromatography column, 25-75% MeCN in water for 22 minutes)

Sources & evidence

ORD record
ord-c3894d411ba846f59476a314cc8afe27
Source dataset
uspto-grants-2015_09
Patent number
US09120758B2

Reaction notes

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