Water → HCID 86652394, compound

HRID 1020999Notes

Reaction equation

HRID 1020999 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]([C:10]1([CH2:24][OH:25])[CH2:14][C:13](=[O:15])[N:12]([C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])[CH2:11]1)=[O:9].CCN(CC)CC.O>C1COCC1>[CH3:6][O:7][C:8]([C:10]1([CH2:24][O:25][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:14][C:13](=[O:15])[N:12]([C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])[CH2:11]1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58218800HCID 58218800, compound

Product 1

HCID 86652394HCID 86652394, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MsCl (105 μL, 1.35 mmol) was added to a cooled (0° C.) solution of 1-(2,6-dimethyl-phenyl)-3-hydroxymethyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step a, 250 mg, 0.9 mmol) and Et3N (375 μL, 2.7 mmol) in THF (5 mL). The resulting reaction mixture was stirred overnight at room temperature. Water (10 mL) was added and extracted with EtOAc (3×25 mL). The combined organic layer was washed with water (50 mL), brine (50 mL), dried (Na2SO4) and evaporated. The obtained crude product 1-(2,6-dimethyl-phenyl)-3-methanesulfonyloxymethyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester was used as such for the next step. LC-MS: Rt (retention time): 1.73 min, MS: (ES) m/z 356.3 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc (3×25 mL)
  3. washThe combined organic layer was washed with water (50 mL), brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-98eabfb2c92841b7ae637ae080402720
Source dataset
uspto-grants-2014_05
Patent number
US08716494B2

Reaction notes

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