Lithium Hydroxide → HCID 11175131, compound

HRID 1264376Notes

Reaction equation

HRID 1264376 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]C(=O)C)[CH2:7][N:6]1[S:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)(=[O:16])=[O:15])=[O:4].[Li+].[OH-]>C1COCC1>[SH:10][C@H:8]1[CH2:7][N:6]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)(=[O:15])=[O:16])[C@H:5]([C:3]([OH:4])=[O:2])[CH2:9]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11153594HCID 11153594, compound

Product 1

HCID 11175131HCID 11175131, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.65 g (2S,4R)-4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester in 220 ml THF were added 220 ml 0.1 N LiOH at 0° C. and the solution was stirred at RT for 1h, concentrated, the inorganic layer was washed with CH2Cl2, acidified and exracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and evaporated yielding (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid as white solid, MS: 337 (MH+).

Workup

  1. concentrationconcentrated
  2. washthe inorganic layer was washed with CH2Cl2
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-636fb0c64cf646118dca70e1f6d12a65
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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