Tetrahydrofuran → HCID 178452623, compound

HRID 1064202Notes

Reaction equation

HRID 1064202 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=C)[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:4])([CH3:3])[CH3:2].[O:25]1CCCC1.C([O-])([O-])=O.[K+].[K+].I([O-])(=O)(=O)=O.[Na+]>C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=[O:25])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 23667635Sodium periodateHCID 136141708(6-Oxo-2-vinyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

Product 1

HCID 178452623HCID 178452623, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of the title compound of Example 164 (48 mg, 0.146 mmol) in 1:1 tetrahydrofuran:H2O (4 mL) was added K2CO3 (30 mg, 0.219 mmol), K2OSO2(OH)4 (7 mg) and K3Fe(CN)6 (72 mg, 0.219 mmol). The mixture was stirred at room temperature for 2 hours whereupon water and ethyl acetate were added. Following extractive work-up, the organic layer was then dried, filtered, and concentrated. The residue was dissolved in 1:1 tetrahydrofuran:H2O (2 mL) and sodium periodate (156 mg, 50.73 mmol) was added. The mixture was stirred at room temperature for 30 min whereupon water and ethyl acetate were added. Following extractive work-up, the organic layer was then dried, filtered, and concentrated. Silica gel chromatography of the residue, eluting with 30% ethyl acetate in hexane gave Intermediate 230(a) as a pale yellow solid (11 mg, 0.034 mmol) in 22% yield.

Workup

  1. additionwere added
  2. customthe organic layer was then dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 1:1 tetrahydrofuran
  6. additionwere added
  7. customthe organic layer was then dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washSilica gel chromatography of the residue, eluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-860dcb08235e4f73a959542eeb555b76
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

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