Lithium hydroxide, monohydrate → HCID 59166748, compound

HRID 1442971Notes

Reaction equation

HRID 1442971 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:4].O[Li].O>C1COCC1>[C:21]([O:20][C:18]([N:6]1[CH2:7][C@@H:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[CH2:9][C@H:5]1[C:3]([OH:4])=[O:2])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59166772HCID 59166772, compound

Product 1

HCID 59166748HCID 59166748, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the (2S,4S)-4-(3-chloro-phenylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (200 mg, 0.58 mmol) in THF (2 ml) was added a solution of LiOH.H2O (73 mg 1.74 mmol), and the reaction stirred at room temperature overnight. The solvent was concentrated in vacuo and the residual aqueous solution washed with DCM (2 ml). The aqueous was then adjusted to pH 5 with saturated aqueous citric acid and re-extracted with DCM (2×10 ml). These combined extracts were dried over MgSO4 and evaporated to give the title compound as a white foam (168 mg, 88%)

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. washthe residual aqueous solution washed with DCM (2 ml)
  3. extractionre-extracted with DCM (2×10 ml)
  4. dry with materialThese combined extracts were dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-7ee60897e9a441ea997c6d2e7ee0ea27
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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