Hydrochloric Acid → HCID 68863559, compound

HRID 1725918Notes

Reaction equation

HRID 1725918 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:24]=[CH:25][C:16]2[C:9](=[CH:8][CH:7]=[CH:22][CH:17]=2)[C:10]=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 68863559HCID 68863559, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 133A (0.50 g, 2.48 mmol) in dichloromethane (8.0 mL) was treated with chlorotrimethylsilane (3.0 mL of 1M solution in CH2Cl2, 2.98 mmol) and pyridine (8.0 mL), stirred at room temperature for 1 hour, treated with methyl 2-(chlorosulfonyl)benzoate (0.873 g, 3.72 mmol), stirred overnight at room temperature treated with 1N HCl (20 mL), and extracted with dichloromethane (2×). The combined organic phases were dried (MgSO4), filtered, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(+)) m/e 400 (M+H)+; (ESI(−)) m/e 398 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.67 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.85 (d, 7.90, 1H), 7.80 (d, 1H), 7.72 (m, 2H), 7.65 (ddd, 1H), 7.56 (m, 2H), 7.50 (d, 1H), 3.80 (s, 3H), 3.78 (s, 3H).

Workup

  1. stirringstirred overnight at room temperature
  2. extractionextracted with dichloromethane (2×)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-592c2f967b004f8590457230b56dd99b
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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