Formic Acid → Tert-butyl {[5-(benzyloxy)pyridin-3-yl](phenylsulfonyl)methyl}carbamate

HRID 526329Notes

Reaction equation

HRID 526329 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=O)[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[C:18]1([S:24]([O-:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:27](=[O:34])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[NH2:28].C(O)=O>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([NH:28][C:27](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium saltHCID 112181335-(Benzyloxy)nicotinaldehyde

Product 1

HCID 71268074Tert-butyl {[5-(benzyloxy)pyridin-3-yl](phenylsulfonyl)methyl}carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 5-(Benzyloxy)pyridine-3-carbaldehyde (3.61 g, 16.9 mmol, Harrowven, D. C. et all Tetrahedron, 2001 57 p. 4447-4454) and benzenesulfinic acid sodium salt (2.7 g, 16.6 mmol) in THF (16.3 mL) was added water (36.3 mL), tert-butyl carbamate (1.94 g, 16.6 mmol) and formic acid (1.9 mL, 49 mmol). The mixture was stirred for 4 day and filtrated. The filtrate was stirred for 2 additional days and filtrated again. The formed precipitates were washed with water and triturated in hexane containing 9% dichloromethane. After filtration the solids were dried in vacuum to yield 3.17 g of tert-butyl {[5-(benzyloxy)pyridin-3-yl](phenylsulfonyl)methyl}carbamate.

Workup

  1. filtrationfiltrated
  2. stirringThe filtrate was stirred for 2 additional days
  3. filtrationfiltrated again
  4. customThe formed precipitates
  5. washwere washed with water
  6. customtriturated in hexane containing 9% dichloromethane
  7. filtrationAfter filtration the solids
  8. customwere dried in vacuum

Sources & evidence

ORD record
ord-bb1e4792aa7745b9b6c0cbf9ad021669
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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