Triethylamine → HCID 7335479, compound

HRID 1976235Notes

Reaction equation

HRID 1976235 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:17])[C@@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27](Cl)(=[O:29])=[O:28])([O-:20])=[O:19]>ClCCl>[CH3:9][O:10][C:11](=[O:17])[C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N+:18]([O-:20])=[O:19])(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 7335479HCID 7335479, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (7.64 g) was added to a suspension of L-proline methyl ester hydrochloride (5 g) and 2-nitrobenzenesulfonyl chloride (7.4 g) in dichloromethane (150 ml), under ice cooling with stirring and the resulting mixture was stirred at room temperature for 17 hours. After water-washing the reaction liquid, it was dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography and then eluted with ethyl acetate/hexane (1/3) to give 9.12 g (yield 96.1%) of the title compound.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 17 hours
  2. washAfter water-washing
  3. customthe reaction liquid, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with ethyl acetate/hexane (1/3)

Sources & evidence

ORD record
ord-1400582f82974d1191d8c3e746a2c6fc
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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