HCID 67462864, compound → HCID 67459475, compound

HRID 554822Notes

Reaction equation

HRID 554822 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])[C:11]([O:13]C)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Na+]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67462864HCID 67462864, compound

Product 1

HCID 67459475HCID 67459475, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of methyl 3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoate (500 mg) in methanol (5 ml), 5N aqueous sodium hydroxide solution (0.84 ml) was added under ice cooling and the mixture was stirred at that temperature for 16 hours. The reaction solution was concentrated in vacuo, then 6N hydrochloric acid was added to make the pH4, and the resultant mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, then the solvent was distilled off in vacuo to obtain the title compound (457.1 mg) as a colorless crystal. The 1H-NMR spectral data matched those of Example 312.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. addition6N hydrochloric acid was added
  3. extractionthe resultant mixture was extracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-6823fe776e5746ad953aa3a42b8ec614
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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