HCID 86704519, compound → HCID 86704521, compound

HRID 633426Notes

Reaction equation

HRID 633426 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[O:15][C:14]2[CH:16]=[CH:17][C:18]([N+:20]([O-])=O)=[CH:19][C:13]=2[N:12]2[N:23]=[N:24][N:25]=[C:11]12)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[OH-].[Pd+2].[OH-].CCO>[Si:28]([O:27][CH2:26][C:10]1([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[O:15][C:14]2[CH:16]=[CH:17][C:18]([NH2:20])=[CH:19][C:13]=2[N:12]2[N:23]=[N:24][N:25]=[C:11]12)([C:31]([CH3:33])([CH3:34])[CH3:32])([CH3:30])[CH3:29]

Participants

4

Reactant 1

HCID 86704519HCID 86704519, compound

Product 1

HCID 86704521HCID 86704521, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4,4-bis(((tert-butyldimethylsilyl)oxy)methyl)-8-nitro-4H-benzo[b]tetrazolo[1,5-d][1,4]oxazine (127 mg, 0.3 mmol), palladium(II) hydroxide on carbon (Aldrich cat. number 212911) (25 mg) and EtOH (10 mL) was hydrogenated at 30 psi for 6 hr. The mixture was then filtered through a short plug of celite, and the filter cake washed with EtOH (3×10 mL). The filtrate was concentrated under vacuum to give the product (yield assumed quantitative=119 mg).

Workup

  1. filtrationThe mixture was then filtered through a short plug of celite
  2. washthe filter cake washed with EtOH (3×10 mL)
  3. concentrationThe filtrate was concentrated under vacuum
  4. customto give
  5. customthe product (yield assumed quantitative=119 mg)

Sources & evidence

ORD record
ord-aa925f5cdaa243f6b992462fcf56a398
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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