Sodium Bicarbonate → HCID 145726187, compound

HRID 1664875Notes

Reaction equation

HRID 1664875 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:15][N:14]2[C:16]([CH:19]=O)=[CH:17][N:18]=[C:13]2[C@H:12]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:11][CH2:10]1.[CH3:29][C:30]([S@:33]([NH2:35])=[O:34])([CH3:32])[CH3:31].C(=O)(O)[O-].[Na+]>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:30]([S:33](/[N:35]=[CH:19]/[C:16]1[N:14]2[CH2:15][C@H:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])[CH2:10][CH2:11][C@@H:12]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[C:13]2=[N:18][CH:17]=1)=[O:34])([CH3:32])([CH3:31])[CH3:29]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 59722730HCID 59722730, compound

Product 1

HCID 145726187HCID 145726187, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Titanium (IV) ethoxide (239 mg, 1.05 mmol) was added to a solution of tert-butyl [(6S,9R)-6-(2,3-difluorophenyl)-3-formyl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-yl]carbamate (205 mg, 0.524 mmol) and (R)-2-methylpropane-2-sulfinamide (79 mg, 0.655 mmol) in tetrahydrofuran (8 mL). The reaction mixture was heated to 60° C. After 6 h, the reaction mixture was allowed to cool to ambient temperature. Saturated sodium bicarbonate was added and the mixture was extracted with dichlormethane (3×). The organic extracts were dried with magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (252 mg). MS 495.2 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionthe mixture was extracted with dichlormethane (3×)
  3. dry with materialThe organic extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-c5f20ee485404f498f366639e1810563
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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