Hydrochloric Acid → HCID 131727572, compound

HRID 2100592Notes

Reaction equation

HRID 2100592 reaction equation
[Cl:1][C:2]1[C:3]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:4]([C@@H:11]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][C@H:12]2[C:23]([O:25]C)=[O:24])[CH:5]=[C:6]([CH2:8][CH2:9][CH3:10])[CH:7]=1.[OH-].[Li+].Cl>C1COCC1.O>[C:19]([O:18][C:16]([N:14]1[CH2:15][C@@H:11]([C:4]2[CH:5]=[C:6]([CH2:8][CH2:9][CH3:10])[CH:7]=[C:2]([Cl:1])[C:3]=2[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C@H:12]([C:23]([OH:25])=[O:24])[CH2:13]1)=[O:17])([CH3:20])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 131727571HCID 131727571, compound

Product 1

HCID 131727572HCID 131727572, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-trans-1-tert-butyl 3-methyl 4-(3-chloro-2-(ethoxycarbonyl)-5-propylphenyl)pyrrolidine-1,3-dicarboxylate (0.78 g, 1.72 mmol) in 20 mL of THF and 10 mL of water was added lithium hydroxide (0.051 g, 2.15 mmol). The reaction was stirred at ambient temperature for 3 h and then was acidified with 1N HCl. The reaction mixture was extracted with EtOAc and the organics were washed with brine, dried (MgSO4) and concentrated to afford 0.75 g (98%) of the title compound as a white foam. LRMS (ES)+: 340.17/342.16 (M+H—BOC)+.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washthe organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-120bdef370e24049a8914f2a3fd5b96b
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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