HCID 86704524, compound → HCID 86704523, compound

HRID 633428Notes

Reaction equation

HRID 633428 reaction equation
[Li]CCCC.CC1C=CC(S(O[CH2:17][C:18]2([CH2:34][OH:35])[O:23][C:22]3[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:21]=3[N:20]3[N:31]=[N:32][N:33]=[C:19]23)(=O)=O)=CC=1>C1COCC1>[N+:28]([C:26]1[CH:25]=[CH:24][C:22]2[O:35][CH2:34][C:18]3([C:19]4[N:20]([N:31]=[N:32][N:33]=4)[C:21]=2[CH:27]=1)[CH2:17][O:23]3)([O-:30])=[O:29]

Participants

4

Reactant 2

HCID 86704524HCID 86704524, compoundHCID 178418339Butyllithium

Product 1

HCID 86704523HCID 86704523, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

nBuLi (1.6 M in hexanes, 110 μL, 0.18 mmol) was added dropwise over 5 min to a stirred solution of (4-(hydroxymethyl)-8-nitro-4H-benzo[b]tetrazolo[1,5-d][1,4]oxazin-4-yl)methyl 4-methylbenzenesulfonate (70 mg, 0.16 mmol) in THF (10 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 1 hr, then heated to reflux and stirred for 2 hr. After allowing to cool, the mixture was concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography using DCM/EtOAc (9:1) as eluent to give the product (16 mg, 38% yield) as a solid.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. stirringstirred for 2 hr
  4. temperatureto cool
  5. concentrationthe mixture was concentrated under vacuum
  6. customto leave a crude residue
  7. customThe residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-14a3cc100f11483788d62dde8482c5f9
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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