Water → (2S,4R)-4-Hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

HRID 1264369Notes

Reaction equation

HRID 1264369 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][NH:5]1.Cl.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[S:22](Cl)(=[O:24])=[O:23].O>C1(C)C=CC=CC=1.C1COCC1>[CH3:1][O:2][C:3]([C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[S:22]([C:13]1[CH:14]=[CH:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=1)(=[O:24])=[O:23])=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 71252-Naphthalenesulfonyl chlorideHCID 114353194-Hydroxy-L-proline methyl ester hydrochloride

Product 1

HCID 7987003(2S,4R)-4-Hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl esterYield 82%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

40 g (220 mmol) of L-hydroxyproline methylester·hydrochloride (twice suspended in toluene and evaporated under reduced pressure to remove water) was suspended in 600 ml hexamethyldisilazane and refluxed for 2 h. The solution was evaporated under reduced pressure and dissolved in 100 ml THF. 49.9 g (220 mmol) of 2-naphthalene-sulphonyl chloride in 200 ml of THF were added slowly and stirred for 16 h at RT. 150 ml H2O were added and after 1h the solvents were evaporated. The residue was partitioned between water/EtOAc (3×), the organic phases were washed with 10% NaCl and dried over Na2SO4 to give 60.4 g (82%) of (2S,4R)-4-Hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester, MS: 335 (M+).

Workup

  1. customevaporated under reduced pressure
  2. customto remove water)
  3. temperaturerefluxed for 2 h
  4. customThe solution was evaporated under reduced pressure
  5. dissolutiondissolved in 100 ml THF
  6. customafter 1h the solvents were evaporated
  7. customThe residue was partitioned between water/EtOAc (3×)
  8. washthe organic phases were washed with 10% NaCl
  9. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-d46f22887f5b4890a2385c779a65bbfc
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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