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Nitric Acid → acetic acid (2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-(4-hydroxy-3-nitro-benzyl)-phenyl]-tetrahydro-pyran-2-ylmethyl ester

HRID 1258832
Notes
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Reaction equation

HRID 1258832 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2].[N+:39]([O-])([OH:41])=[O:40]>ClC(Cl)C.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[C:31]([N+:39]([O-:41])=[O:40])[CH:32]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 67115824(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4- hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Product 1

HCID 67115761acetic acid (2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-(4-hydroxy-3-nitro-benzyl)-phenyl]-tetrahydro-pyran-2-ylmethyl ester

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium Bromide
Catalyst
HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of compound prepared in step I (2 g, 3.64 mmol) in dichloroethane (20 mL) was added TBAB (117 mg, 0.364 mmol), 6% aqueous nitric acid (20 mmol) at 0-5° C. and stirred at room temperature for 4 h. Organic layer was separated, washed with water and brine and concentrated to furnish crude acetic acid (2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-(4-hydroxy-3-nitro-benzyl)-phenyl]-tetrahydro-pyran-2-ylmethyl ester which was further purified by column chromatography (1.5 g)

Workup

  1. customOrganic layer was separated
  2. washwashed with water and brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5425041712d546359266a435e88a64ac
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466114B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes