Hydrochloric Acid → (2S,4S)-1-[(benzyloxy)carbonyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinecarboxylic acid

HRID 1053811Notes

Reaction equation

HRID 1053811 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C@@H:11]2[CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[C@H:13]([C:26]([O:28]C)=[O:27])[CH2:12]2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[OH-].[Li+].Cl>O1CCCC1.O>[CH2:19]([O:18][C:16]([N:14]1[CH2:15][C@@H:11]([N:8]2[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]2)[CH2:12][C@H:13]1[C:26]([OH:28])=[O:27])=[O:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 1317362981-benzyl 2-methyl (2S,4S)-4-[4-(methylsulfonyl)-1-piperazinyl]-1,2-pyrrolidinedicarboxylate

Product 1

HCID 118107654(2S,4S)-1-[(benzyloxy)carbonyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinecarboxylic acidYield 65.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound prepared in Example 3 (0.90 g, 2.11 mmol) in tetrahydrofuran (20 mL) and water (20 mL) at 0° C. was added lithium hydroxide (0.203 g, 8.4 mmol). The reaction was warmed to room temperature and stirred overnight. The reaction mixture was carefully acidified to pH 5 with 2 M hydrochloric acid. The aqueous solution was extracted with ethyl acetate (2×300 mL) and the combined organic extracts were dried and concentrated to give the title compound (0.565 g, 65%) as a white solid.

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate (2×300 mL)
  2. customthe combined organic extracts were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9f5720a05d414e0994d5aaeb6c7c2942
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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