Triethylamine → HCID 59560182, compound

HRID 1643655Notes

Reaction equation

HRID 1643655 reaction equation
CCN(CC)CC.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH3:13][O:14][C:15]([C:17]1[CH:27]=[C:26]([O:28][CH:29]2[CH2:32][NH:31][CH2:30]2)[C:20]2[CH2:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=2[CH:18]=1)=[O:16]>C(Cl)Cl>[CH3:13][O:14][C:15]([C:17]1[CH:27]=[C:26]([O:28][CH:29]2[CH2:30][N:31]([S:9]([CH3:8])(=[O:11])=[O:10])[CH2:32]2)[C:20]2[CH2:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=2[CH:18]=1)=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59559971HCID 59559971, compound

Product 1

HCID 59560182HCID 59560182, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et3N (400 mg, 2.87 mmol) and methane sulfonyl chloride (75 uL, 0.97 mmol) were added to a solution of 4-(azetidin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (193c) (303 mg, 0.97 mmol) in CH2Cl2 (15 mL). The mixture was stirred at room temperature for 2 hr, quenched with 1N aqueous HCl (60 mL) and extracted with CH2Cl2 (60 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatograph to give a white solid (197 mg, 57% yield). 1H NMR (400 MHz, CDCl3) δ 7.10 (s, 1 H) 6.75 (s, 1 H) 5.02 (d, J=6.06 Hz, 1 H) 4.34 (dd, J=8.46, 6.69 Hz, 2 H) 4.08 (dd, J=8.72, 4.93 Hz, 2 H) 3.89 (s, 3 H) 3.00 (s, 2 H) 2.93 (s, 3 H) 1.50 (s, 6 H).

Workup

  1. customquenched with 1N aqueous HCl (60 mL)
  2. extractionextracted with CH2Cl2 (60 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatograph

Sources & evidence

ORD record
ord-5d7a15873acd4466a7b92e06c40ccf1a
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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