Triphenylphosphine → Benzyl [2-(chlorosulfonyl)ethyl]carbamate

HRID 1179298Notes

Reaction equation

HRID 1179298 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:20]([Cl:24])(Cl)(=[O:22])=[O:21].[CH2:25]([O:32][C:33]([NH:35][CH2:36][CH2:37]S([O-])(=O)=O)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Na+]>C(Cl)Cl.CCOC(C)=O>[Cl:24][S:20]([CH2:37][CH2:36][NH:35][C:33](=[O:34])[O:32][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 24648Sulfuryl chlorideHCID 57345279HCID 57345279, compound

Product 1

HCID 13255033Benzyl [2-(chlorosulfonyl)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

This compound was prepared using the method of T. S. Widlanski and J. Huang, Tet. Lett. 1992, 33: 2657. A solution of triphenylphosphine (17.6 g, 67.4 mmol) in dry CH2Cl2 (90 mL) was cooled to zero degrees C. under nitrogen and treated with neat sulfuryl chloride (5.96 mL, 74.2 mmol) to give a yellow solution. The solution was recooled to 5 degrees C. and crushed solid sodium 2-{[(benzyloxy)carbonyl]amino}ethanesulfonate (12 g, 42.6 mmol) prepared as described by Bricas et al., Biochimica et Biophysica Acta 1955, (18), 358, was added all at once to give a white suspension. The reaction was allowed to warm to room temperature and stirred for 3 hours. The volatiles were removed in vacuo to give an oily/solid residue that was suspended in EtOAc and added to the top of a silica column (3 inches by 150 mm) packed in EtOAc. The product was eluted with EtOAc and the UV active fractions were combined and evaporated to give the product as a white solid.

Workup

  1. customThis compound was prepared
  2. customto give a yellow solution
  3. customwas recooled to 5 degrees C
  4. customprepared
  5. additionwas added all at once
  6. customto give a white suspension
  7. customThe volatiles were removed in vacuo
  8. customto give an oily/solid residue that
  9. additionadded to the top of a silica column (3 inches by 150 mm)
  10. washThe product was eluted with EtOAc
  11. customevaporated

Sources & evidence

ORD record
ord-699d4e8e6f29473cb7337f3d135a6074
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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