Hydrochloric Acid → HCID 10872694, compound

HRID 380359Notes

Reaction equation

HRID 380359 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH2:10][C@@H:11]([N:18]([C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=2)[CH3:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1.[OH-].[Na+].Cl>CO>[CH3:1][O:2][CH2:3][O:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH2:10][C@@H:11]([N:18]([C:20]2[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:28][CH:29]=2)[CH3:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15521000HCID 15521000, compound

Product 1

HCID 10872694HCID 10872694, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of methyl 4-{N-[2-(3-(S)-methoxymethoxypyrrolidin-1-yl)-1-(S)-phenylethyl]-N-methylamino}benzoate (1.99 g, 5.00 mmol) and 4N-NaOH (12.5 ml, 50.0 mmol) in MeOH (35 ml) was stirred at 75° C. for 3 h. The mixture was neutrallized with 5N-HCl at 0° C. The solvent was removed in vacuo. CH2Cl2 was added to the residue and insoluble solid was removed by filtration. The filtrate was concentrated to give 2.04 g (quant) of pale brown amorphous.

Workup

  1. customThe solvent was removed in vacuo
  2. additionCH2Cl2 was added to the residue and insoluble solid
  3. customwas removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customto give 2.04 g (quant) of pale brown amorphous

Sources & evidence

ORD record
ord-b989d2ce4d824b75b61e12c1a9cb6724
Source dataset
uspto-grants-2001_10
Patent number
US06303602B1

Reaction notes

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