Benzyl chloroformate → Methyl 4-({[(benzyloxy)carbonyl]amino}sulfonyl)benzoate

HRID 860417Notes

Reaction equation

HRID 860417 reaction equation
[NH2:1][S:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:28][C:29](Cl)=[O:30])=[CH:23][CH:22]=1>C(COC)OC>[CH2:27]([O:28][C:29]([NH:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=1)(=[O:3])=[O:4])=[O:30])[C:24]1[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 89847Methyl 4-sulphamoylbenzoate

Product 1

HCID 57444531Methyl 4-({[(benzyloxy)carbonyl]amino}sulfonyl)benzoateYield 40.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A mixture of methyl 4-(aminosulfonyl)benzoate (5.10 g) and potassium carbonate (6.55 g) in dimethoxyethane (50 mL) was refluxed for 5 minutes. After cooling the mixture, a solution of benzyl chloridocarbonate (5.25 g) in dimethoxyethane (30 mL), and the resulting mixture was refluxed for 1 hour. The reaction was quenched by adding 1N hydrochloric acid (100 mL). The mixture was extracted with ethyl acetate (200 mL), and the organic layer was washed with brine, dried over magnesium sulfate, and evaporated to give a pale yellow oil, which was solidified upon standing. The solid was triturated in diisopropyl ether (30 mL) to give methyl 4-({[(benzyloxy)carbonyl]amino}sulfonyl)benzoate as a white powder (3.38 g).

Workup

  1. temperaturewas refluxed for 5 minutes
  2. temperatureAfter cooling the mixture
  3. customThe reaction was quenched
  4. additionby adding 1N hydrochloric acid (100 mL)
  5. extractionThe mixture was extracted with ethyl acetate (200 mL)
  6. washthe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto give a pale yellow oil, which
  10. customThe solid was triturated in diisopropyl ether (30 mL)

Sources & evidence

ORD record
ord-736265cd995d4267a52dc15d729d1bb6
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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