Hydrochloric Acid → tert-Butyl ((diphenylphosphoryl)methyl)sulfonylcarbamate

HRID 2036830Notes

Reaction equation

HRID 2036830 reaction equation
[CH3:1][S:2]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:4])=[O:3].[Li+].CC([N-]C(C)C)C.[C:21]1([P:27](Cl)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>C1COCC1.C(OCC)(=O)C.O>[C:8]([O:7][C:6](=[O:12])[NH:5][S:2]([CH2:1][P:27]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:28])(=[O:4])=[O:3])([CH3:9])([CH3:11])[CH3:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73910Diphenylphosphinic chlorideHCID 2724682Lithium diisopropylamideHCID 10081367tert-Butyl methylsulfonylcarbamate

Product 1

HCID 11395320tert-Butyl ((diphenylphosphoryl)methyl)sulfonylcarbamateYield 73.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl methylsulfonylcarbamate (2 g, 10 mmol) in THF (25 mL) at −78° C. was added LDA (2 M in THF, 15.4 mL, 30.7 mmol). Upon completion of addition, the reaction mixture stirred for 10 min and then diphenylphosphinic chloride (2.42 g, 10.2 mmol) was added drop wise to the reaction at −78° C. After 90 min, water (100 mL) was added and the reaction mixture was diluted with ethyl acetate (250 mL). The aqueous layer was adjusted to pH 5 with 5% aqueous HCl. The white precipitate that formed was filtered and the solid dried in vacuo to give tert-butyl(diphenylphosphoryl)methylsulfonylcarbamate (2.9 g, 72% yield) as a white solid.

Workup

  1. additionUpon completion of addition
  2. customwise to the reaction at −78° C
  3. waitAfter 90 min
  4. customThe white precipitate that formed
  5. filtrationwas filtered
  6. customthe solid dried in vacuo

Sources & evidence

ORD record
ord-ea044f5cb37a42a884702011d77abe90
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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