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Benzyl azide → HCID 136384027, compound

HRID 1847251
Notes
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Reaction equation

HRID 1847251 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[N:15][S:14][C:9]2=[C:10]([C:12]#[CH:13])[N:11]=1)=[O:5])[CH3:2].[CH2:25]([N:32]=[N+:33]=[N-:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CCO.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:16]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)=[N:15][S:14][C:9]2=[C:10]([C:12]2[N:34]=[N:33][N:32]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:13]=2)[N:11]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 136413571HCID 136413571, compound

Product 1

HCID 136384027HCID 136384027, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a mixture of 3-(4-chloro-phenyl)-7-ethynyl-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (0.106 mmol) and CH2Cl2/H2O (1/1, 0.70 mL) was added benzylazide (0.117 mmol), CuSO4.5H2O (0.0053 mmol) and sodium L-ascorbate (0.0159 mmol). The mixture was stirred at rt for 16 h before it was partitioned between H2O (20 mL) and CH2Cl2 (20 mL). The aqueous phase was then extracted with CH2Cl2 (2×15 mL). The combined organic layers were washed with brine and water, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 0-20% EtOAc/CH2Cl2, to give the title compound (40 mg) as a white solid: MS (m/z) 492.1 (M+1).

Workup

  1. customwas partitioned between H2O (20 mL) and CH2Cl2 (20 mL)
  2. extractionThe aqueous phase was then extracted with CH2Cl2 (2×15 mL)
  3. washThe combined organic layers were washed with brine and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-1af8a708e7b6435d92151c5ba4275f62
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952160B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes