Benzyl Alcohol → HCID 178523954, compound

HRID 2272638Notes

Reaction equation

HRID 2272638 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].C(O)[C:34]1[CH:39]=[CH:38]C=[CH:36][CH:35]=1.Cl.O1CCOCC1>>[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])[C:2]1[CH:38]=[CH:39][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178472580HCID 178472580, compound

Product 1

HCID 178523954HCID 178523954, compoundYield 39.9%

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 benzyl alcohol (20 mL, 100 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 evaporated under reduced pressure and purified (Interchim C18 reverse phase chromatography column, 30-95% MeCN in water with 0.05% TFA). The clean fractions were combined, lyophilized and purified to yield the title compound (688 mg; purity 98%). MS m/z [M+H]+ calc'd for C27H24ClN3O6, 522.14. found 522.2.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. custompurified (Interchim C18 reverse phase chromatography column, 30-95% MeCN in water with 0.05% TFA)
  3. custompurified

Sources & evidence

ORD record
ord-c1c94dc5baa344eca33b443fcdeafef4
Source dataset
uspto-grants-2015_09
Patent number
US09120758B2

Reaction notes

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