Methyl N-(triethylammoniosulfonyl)carbamate → HCID 71293436, compound

HRID 2362313Notes

Reaction equation

HRID 2362313 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[C:15](=[O:18])[NH:16][N:17]=[C:13]3[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:11]([CH3:29])=[C:10]2[C:30]([NH2:32])=O)=[CH:5][CH:4]=1)#[N:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[C:15](=[O:18])[NH:16][N:17]=[C:13]3[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:11]([CH3:29])=[C:10]2[C:30]#[N:32])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 71293427HCID 71293427, compound

Product 1

HCID 71293436HCID 71293436, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 13 (92 mg, 0.209 mmol) was dissolved in THF (8 mL), and Burgess reagent (150 mg, 0.63 mmol) was added. The reaction mixture was stirred at RT for 30 mins and was then partitioned between EtOAc and water. The organic layer was separated, and the aqueous layer further extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with 80% EtOAc in cyclohexane as eluent to yield a white solid. Further purification was carried out by reverse phase HPLC using a gradient of 40-98% MeCN in water (+0.1% formic acid) to yield the title compound as a white solid (34 mg).

Workup

  1. customwas then partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer further extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe resulting residue was purified by silica gel chromatography
  8. washeluting with 80% EtOAc in cyclohexane as eluent
  9. customto yield a white solid
  10. customFurther purification

Sources & evidence

ORD record
ord-884163f011884674b57c23c02f44b96f
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

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