Water → HCID 21350206, compound

HRID 1359375Notes

Reaction equation

HRID 1359375 reaction equation
[CH2:1]([C:8]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[CH:12][CH:11]=[C:10]([N:18]2[CH2:22][CH2:21][C@H:20]([OH:23])[C:19]2=[O:24])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:25]([C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1)([O-:27])=[O:26].C(N(CC)CC)C.O>C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[CH2:1]([C:8]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[CH:12][CH:11]=[C:10]([N:18]2[CH2:22][CH2:21][C@H:20]([O:23][S:34]([C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([N+:25]([O-:27])=[O:26])[CH:29]=3)(=[O:35])=[O:36])[C:19]2=[O:24])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 21350207HCID 21350207, compound

Product 1

HCID 21350206HCID 21350206, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.2 g of 2-benzyl-3-methoxymethyloxy-6-[(3S)-3-hydroxy-2-pyrrolidinone-1-yl]pyridine (Example 138a) was dissolved in 20 ml of ethyl acetate, and 2.3 g of 3-nitrobenzenesulfonyl chloride, 183 mg of 4-dimethylaminopyridine and 3 ml of triethylamine were added thereto, followed by stirring at room temperature overnight. Then, water was added thereto, and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 25-33% ethyl acetate/hexane as an eluent, to give 3.5 g of the target compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was further washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-5744d401a1864fac8a3da27c60111189
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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