4-Chlorobenzenesulfonyl chloride → (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine

HRID 257965Notes

Reaction equation

HRID 257965 reaction equation
[NH2:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>ClCCl>[C:10]([O:9][C:7]([N:5]1[CH2:6][C@H:2]([NH:1][S:32]([C:29]2[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[CH2:3][C@H:4]1[C:14]([O:16][CH3:17])=[O:15])=[O:8])([CH3:11])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 70099181-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate

Product 1

HCID 14772685(2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidineYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-4-amino-1-t-butoxycarbonyl-2-methoxycarbonylpyrrolidine (6.04 g) in dichloromethane (60 ml) were added triethylamine (3.44 ml) and p-chlorobenzenesulfonyl chloride (6.26 g) in an ice bath. After being stirred at room temperature overnight, the solution was washed successively with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was crystallized from n-hexane to give (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine (9.13 g) as a pale yellow crystal.

Workup

  1. washthe solution was washed successively with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-78f39a20228d4fc4ab5f2b6e0a20e572
Source dataset
uspto-grants-1993_11
Patent number
US05264453

Reaction notes

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