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

HRID 526322Notes

Reaction equation

HRID 526322 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)[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:12]([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:14]=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 743423-BenzyloxybenzaldehydeHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 71268083Tert-butyl {[3-(benzyloxy)phenyl](phenylsulfonyl)methyl}carbamateYield 67.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-(benzyloxy)benzaldehyde (5 g, 23.6 mmol) and benzenesulfinic acid sodium salt (3.9 g, 23.6 mmol) in THF (23 mL) was added water (51.5 mL), tert-butyl carbamate (2.76 g, 23.6 mmol) and formic acid (2.66 mL, 70 mmol). The mixture was stirred for 4 day and filtrated. The precipitate was washed with water and triturated in hexane containing 9% dichloromethane. After filtration the solids were dried in vacuum to yield 7.24 g of tert-butyl {[3-(benzyloxy)phenyl](phenylsulfonyl)methyl}carbamate.

Workup

  1. filtrationfiltrated
  2. washThe precipitate was washed with water
  3. customtriturated in hexane containing 9% dichloromethane
  4. filtrationAfter filtration the solids
  5. customwere dried in vacuum

Sources & evidence

ORD record
ord-a696aa5698854830bc9c51150fe1ed6d
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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