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1,2-Dichloroethane → 2-Deoxyglucose

HRID 1434490
Notes
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Reaction equation

HRID 1434490 reaction equation
[OH-].[Na+].C1C(=O)N(O)C(=O)C1S([O-])(=O)=O.[Na+].C(Cl)CCl.Cl.[OH:21][CH:22]1[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]1N>O>[O:21]=[CH:22][CH2:23][C@H:25]([C@@H:27]([C@@H:29]([CH2:31][OH:32])[OH:30])[OH:28])[OH:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14798Sodium HydroxideHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochlorideHCID 3520574n-hydroxysulfosuccinimide sodium salt

Product 1

HCID 1082232-Deoxyglucose

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Sodium hydroxide (1N, 1 ml) was added to a stirred solution of EC (110 mg, 0.41 mmol) in water (5 ml). To this colorless solution, sulfo-NHS (241.6 mg, 1.12 mmol) and EDC (218.8 mg, 1.15 mmol) were added. D-Glucosamine hydrochloride salt (356.8 mg, 1.65 mmol) was then added. The mixture was stirred at room temperature for 24 hours. The mixture was dialyzed for 48 hours using Spectra/POR molecular porous membrane with cut-off at 500 (Spectrum Medical Industries Inc., Houston, Tex.). After dialysis, the product was frozen dried using lyophilizer (Labconco, Kansas City, Mo.). The product in the salt form weighed 568.8 mg. The synthetic scheme is shown in FIG. 59. The structure was confirmed by mass spectrometry (FIG. 60) and proton NMR (FIGS. 61 and 62). Radiochemical purity of 99mTc-EC-DG was 100% as determined by radio-TLC (FIG. 63) and HPLC (FIGS. 64 and 65) analysis.

Workup

  1. customThe mixture was dialyzed for 48 hours
  2. customAfter dialysis
  3. temperaturethe product was frozen
  4. customdried

Sources & evidence

ORD record
ord-5b7d251d8fb24b458f7371290328ec1c
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07615208B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes