Sulfuryl chloride → HCID 86598003, compound

HRID 2215290Notes

Reaction equation

HRID 2215290 reaction equation
[C:1](=[O:19])(SCC)[O:2][O:3][CH:4]([O:8][C:9]([CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[CH2:5][CH2:6][CH3:7].S(Cl)([Cl:23])(=O)=O>C(Cl)Cl>[Cl:23][C:1]([O:2][O:3][CH:4]([O:8][C:9]([CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[CH2:5][CH2:6][CH3:7])=[O:19]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 86598001HCID 86598001, compound

Product 1

HCID 86598003HCID 86598003, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (67) (1.83 g, 6.34 mmol) in CH2Cl2 at 0° C. was treated with sulfuryl chloride (0.62 mL, 7.61 mmol) under N2 for 10 min, then the reaction mixture was concentrated to dryness in vacuo to afford crude (1-cyclopentanecarbonyloxy-butoxy) chloroformate in quantitative yield. The chloroformate was dissolved in CH2Cl2, and was added to a mixture of N-hydroxysuccinimide (1.09 g, 9.51 mmol) and pyridine (1.28 mL, 15.8 mmol) in CH2Cl2 at 0° C. The reaction mixture was stirred at 0° C. for 1 h, then was washed with water, dilute HCl and brine and dried over Na2SO4. After removal of solvent in vacuo the title N-hydroxysuccinimidyl carbonate (68) was obtained in quantitative yield, and was used in the subsequent step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-d5e8c3e06c4f40d2a52e85776e1797a9
Source dataset
uspto-grants-2006_09
Patent number
US07109239B2

Reaction notes

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