Methyl N-(triethylammoniosulfonyl)carbamate → HCID 66727508, compound

HRID 559698Notes

Reaction equation

HRID 559698 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@@H:4]([NH:8][C:9](=O)[CH:10]([NH:13][C:14]([C:16]1[C:17]2[CH:24]=[N:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:18]=2[CH:19]=[N:20][CH:21]=1)=[O:15])[CH2:11][CH3:12])[C@H:5]([OH:7])[CH3:6].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:1][O:2][C:3]([C@@H:4]1[C@H:5]([CH3:6])[O:7][C:9]([CH:10]([NH:13][C:14]([C:16]2[C:17]3[CH:24]=[N:23][N:22]([C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)[C:18]=3[CH:19]=[N:20][CH:21]=2)=[O:15])[CH2:11][CH3:12])=[N:8]1)=[O:33]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59278349HCID 59278349, compound

Product 1

HCID 66727508HCID 66727508, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,3R)-2-(2-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-butyrylamino)-3-hydroxy-butyric acid methyl ester (0.900 g, 1.96 mmol) in THF (20.0 mL) was added Burgess reagent (0.586 g, 2.46 mmol). The mixture was warmed at reflux for 23 hours. The mixture was then concentrated in vacuo, dissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-10% methanol in ethyl acetate to afford (4S,5S)-2-(1-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester as white foam.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureat reflux for 23 hours
  3. concentrationThe mixture was then concentrated in vacuo
  4. dissolutiondissolved in ethyl acetate (100 mL)
  5. washwashed with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with a gradient of 0-10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-232d3c21a3a949f98d1f0dd314a40f5d
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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