Hydrochloric Acid → HCID 11668533, compound

HRID 1725954Notes

Reaction equation

HRID 1725954 reaction equation
Cl[Si](C)(C)C.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[S:13]([C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:15])=[O:14].Cl>ClCCl>[CH3:21][O:20][C:18]([C:17]1[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=1[S:13]([NH:6][C:11]1[CH:10]=[CH:9][C:8]2[CH2:25][CH2:24][CH2:23][CH2:22][C:7]=2[C:17]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:15])=[O:14])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl ester

Product 1

HCID 11668533HCID 11668533, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 418A (1.81 g, 8.35 mmol) in dichloromethane (25.5 mL) was treated with chlorotrimethylsilane (6.7 mL of 1M CH2Cl2 solution, 16.7 mmol) and pyridine (25.5 mL), stirred at room temperature for 10 minutes, treated with methyl 2-(chlorosulfonyl)benzoate (2.61 g, 11.11 mmol), stirred overnight at room temperature, and treated with 1N HCl (50 mL). The aqueous phase was extracted with dichloromethane two times and the combined organic phases were washed with water and brine, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(+)) m/e 404 (M+H)+; 480 (M+Na)+; (ESI(−)) m/e 402 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.14 (s, 1H), 7.77-7.65 (m, 4H), 7.12 (d, 1H), 6.98 (d, 1H), 3.01 (s, 3H), 3.63 (s, 3H), 2.68 (br s, 2H), 2.53 (br s, 2H), 1.66 (br m, 4H).

Workup

  1. stirringstirred overnight at room temperature
  2. extractionThe aqueous phase was extracted with dichloromethane two times
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6592ea8ddb3c447cbc007b2060fef2cc
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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