Sodium Hydroxide → HCID 70039904, compound

HRID 280786Notes

Reaction equation

HRID 280786 reaction equation
C[O:2][C:3](=[O:43])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:42])[CH2:10][N:11]([C:21](=[O:41])[C@H:22]([CH3:40])[NH:23][P:24]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25])[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1.[OH-].[Na+]>CC(C)=O.O>[CH2:26]([P:24]([NH:23][C@H:22]([C:21]([N:11]([CH:12]1[CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20]1)[CH2:10][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[C:3]([OH:43])=[O:2])=[O:42])=[O:41])[CH3:40])([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:25])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86739653HCID 86739653, compound

Product 1

HCID 70039904HCID 70039904, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Dibenzylphosphoryl-L-alanyl-N-(2-indanyl)glycyl-L-proline methylester (0.79 g, 1.2 m mole) was dissolved in acetone (5 ml), and sodium hydroxide (0.15 g, 3.8 m mole) in water (4 ml) solution was added thereto while cooling in the ice bath. The mixture was stirred for 1 hour. To this solution water (100 ml) was added, and thereafter this thus formed solution was washed with ethyl ether (50 ml). the ether washed solution was neutralized with 1N hydrochloric acid, and therefrom the desired product was extracted with ethyl acetate. The thus extracted solution was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain an oily dibenzylphosphoryl-L-alanyl-N-(2-indanyl)glycyl-L-proline (0.77 g, yield: 99.7%).

Workup

  1. washthis thus formed solution was washed with ethyl ether (50 ml)
  2. extractionthe desired product was extracted with ethyl acetate
  3. dry with materialThe thus extracted solution was dried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-acf4e563d8784b20b8fe8b72f8de9bd3
Source dataset
uspto-grants-1986_05
Patent number
US04590178

Reaction notes

Loading…