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

HRID 541503
Notes
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Reaction equation

HRID 541503 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-butoxycarbonylhydrazino]-2-hydroxypropionic 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-e39ff5c7e89e4cbba59ae88abc4e3eda
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871792B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes