Methanol → HCID 846127, compound

HRID 1655714Notes

Reaction equation

HRID 1655714 reaction equation
[CH2:1]([C@H:8]([N:13]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]1[CH3:19])[C:9]([O:11]C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CO>O>[CH2:1]([C@H:8]([N:13]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]1[CH3:19])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 2100825HCID 2100825, compound

Product 1

HCID 846127HCID 846127, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-phenylalanyl methyl ester hydrochloride was converted into the corresponding free base by shaking with a sodium bicarbonate solution in ether and heated to 100° for 2.5 hours in glacial acetic acid with acetonylacetone. Thereafter, the solvent was evaporated and the residue was filtered with toluene over silica gel, to obtain methyl (S)-α-benzyl-2,5-dimethylpyrrole-1-acetate, MS: 258 (M+H)+. The ester so obtained was allowed to stand at room temperature for 1.5 hours with 1N sodium hydroxide solution in a 9:1 mixture of methanol and water. After extracting the aqueous solution with ether and washing the organic phase, there was obtained (S)-α-benzyl-2,5-dimethylpyrrole-1-acetic acid, MS: 244 (M+H)+, which was used directly in the next step.

Workup

  1. extractionAfter extracting the aqueous solution with ether
  2. washwashing the organic phase

Sources & evidence

ORD record
ord-7bb762523a1f40d5959dbaba7980f0ca
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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