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Sodium sulfate decahydrate → HCID 68092388, compound

HRID 1772048
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Reaction equation

HRID 1772048 reaction equation
[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[O:7][CH2:8][CH2:9][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11]=3[CH:12]=[CH:13]2)=[N:4][C:3]=1[C:22](OCC)=[O:23].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:23][CH2:22][C:3]1[N:4]=[C:5]2[N:14]([C:2]=1[CH3:1])[CH:13]=[CH:12][C:11]1[N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][CH2:8][O:7][C:6]2=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 68089378HCID 68089378, compound

Product 1

HCID 68092388HCID 68092388, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10-tert-butyl 4-ethyl 5-methyl-13-oxa-3,6,10-triazatricyclo[7.4.0.0{2,6}]trideca-1(9),2,4,7-tetraene-4,10-dicarboxylate (757 mg, 2.09 mmol) in 50 mL of THF was added LAH (2.364 g, 6.27 mmol) at 0° C. The mixture was stirred for 3 h at room temperature. To the mixture was added sodium sulfate decahydrate (257 mg) and the mixture was stirred for 15 min at room temperature. The solid was removed by filtration and the filtrate was concentrated. The residue was purified by reverse phase column chromatography (eluting with 15% acetonitrile in water, with 0.1% NH3.H2O) to give tert-butyl 4-(hydroxymethyl)-5-methyl-13-oxa-3,6,10-triazatricyclo[7.4.0.0{2,6}]trideca-1(9),2,4,7-tetraene-10-carboxylate (630 mg, 94% yield) as a white solid. ESI MS: m/z 320 [M+H]+.

Workup

  1. stirringthe mixture was stirred for 15 min at room temperature
  2. customThe solid was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by reverse phase column chromatography (eluting with 15% acetonitrile in water, with 0.1% NH3.H2O)

Sources & evidence

ORD record
ord-f5eded259c2b4ceeaf4505fadbee7efe
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249162B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes