1,4-Dioxane → (R)-3-[N-(4-Bromobenzyl)hydrazino]-2-hydroxypropionic Acid Methyl Ester

HRID 2272640Notes

Reaction equation

HRID 2272640 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([OH:23])[CH2:5][N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1)[NH:7]C(OC(C)(C)C)=O.O1CCOCC1>CC#N.Cl>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([OH:23])[CH2:5][N:6]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][CH:21]=1)[NH2:7]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 67972599(R)-3-[N-(4-Bromobenzyl)-N'-t-butoxycarbonylhydrazino]-2-hydroxypropionic acid methyl ester

Product 1

HCID 67972305(R)-3-[N-(4-Bromobenzyl)hydrazino]-2-hydroxypropionic Acid Methyl EsterYield 99%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

(R)-3-[N-(4-Bromobenzyl)-N′-t-butoxycarbonyl-hydrazino]-2-hydroxy-propionic acid methyl ester (1.1 g, 2.8 mmol) was dissolved in MeCN (10 mL) and of 4N HCl in dioxane (6 mL, 20 mmol). The mixture was stirred at room temperature until deprotection was complete (1 hour). The precipitate was filtered and dried to yield the title compound (840 mg) as an HCl salt.

Workup

  1. custom(1 hour)
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-77fd435bb76b421c94ca9dd905c0c22b
Source dataset
uspto-grants-2015_09
Patent number
US09120758B2

Reaction notes

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