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

HRID 1043987
Notes
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Reaction equation

HRID 1043987 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent

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-662938f7c7ef4c428444035586309d54
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563512B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes