HCID 22858687, compound → HCID 22858688, compound

HRID 2396143Notes

Reaction equation

HRID 2396143 reaction equation
C([O:8][C:9](=[O:35])[C@H:10]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[NH:11][C:12]([N:14]([CH2:16][CH2:17][N:18]([C:20]([N:22]1[CH2:27][CH2:26][S:25][CH2:24][CH2:23]1)=[O:21])[CH3:19])[CH3:15])=[O:13])C1C=CC=CC=1>CO.[OH-].[Na+]>[S:25]1[CH2:26][CH2:27][N:22]([C:20]([N:18]([CH2:17][CH2:16][N:14]([CH3:15])[C:12]([NH:11][C@H:10]([C:9]([OH:35])=[O:8])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:13])[CH3:19])=[O:21])[CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 22858687HCID 22858687, compound

Product 1

HCID 22858688HCID 22858688, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of N-[N-[2-(N-thiomorpholinocarbonyl-N-methylamino)ethyl]-N-methylaminocarbonyl]-L-phenylalanine benzyl ester (1.50 g) in methanol (30 ml) was added in 1N sodium hydroxide aqueous solution (6 ml) at ambient temperature. After being stirred for 3 hours at the same temperature, the solution was concentrated in vacuo. The residue was dissolved in ethyl acetate (50 ml) and the solution was washed with 5% hydrochloric acid and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give N-[N-[2-(N-thiomorpholinocarbonyl-N-methylamino)ethyl]-N-methylaminocarbonyl]-L-phenylalanine (1.14 g) as an oil. Rf : 0.31 ( chloroform:methanol:acetic acid, 16:1:1, V/V)

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  3. washthe solution was washed with 5% hydrochloric acid and brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b777a9636c4b4508bf0efb7453704177
Source dataset
uspto-grants-1996_02
Patent number
US05491132

Reaction notes

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