Sodium Hydroxide → HCID 70039904, compound

HRID 485591Notes

Reaction equation

HRID 485591 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

Dibenzylphosphory-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 the solution water (100 ml) was added, and thereafter it was washed with ethyl ether (50 ml). It was neutralized with 1N hydrochloric acid, and therefrom the desired product was extracted with ethyl acetate. 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. washit was washed with ethyl ether (50 ml)
  2. extractionthe desired product was extracted with ethyl acetate
  3. dry with materialThus extracted solution was dried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6083c1e6f3a74249a232bbe8598f28c9
Source dataset
uspto-grants-1985_08
Patent number
US04536395

Reaction notes

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