Water → HCID 70040089, compound

HRID 2418524Notes

Reaction equation

HRID 2418524 reaction equation
C[O:2][C:3](=[O:40])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:39])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:38])[C@H:16]([CH2:34][CH2:35][S:36][CH3:37])[NH:17][P:18]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19].[OH-].[Na+].O>CC(C)=O>[CH2:20]([P:18]([NH:17][C@H:16]([C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[C:3]([OH:40])=[O:2])=[O:39])=[O:38])[CH2:34][CH2:35][S:36][CH3:37])([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:19])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86739655HCID 86739655, compound

Product 1

HCID 70040089HCID 70040089, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dibenzylphosphoryl-L-methionyl-L-prolyl-L-proline methylester (1.87 g, 3.0 m mole) was dissolved in acetone (18 ml), and 1N sodium hydroxide (4.5 ml) was added thereto under cooling and the mixture was stirred for 4 hours. To the solution, water (100 ml) was added, and the solution was washed with diethyl ether. Ethyl acetate (200 ml) was added thereto and the mixture was adjusted to pH 2 with 1N hydrochloric acid while stirring strongly. The ethyl acetate phase was separated and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain an oily dibenzylphosphoryl-L-methionyl-L-prolyl-L-proline (1.81 g, yield: 99.1%). All of the thus obtained product (3.0 m mole) was dissolved in ethanol (15 ml) and a L-arginine (0.58 g, 3.0 m mole) water (5 ml) solution was added thereto. The solvent was evaporated, water was added thereto, and the thus obtained solution was freeze-dried to obtain dibenzylphosphoryl-L-methionyl-L-prolyl-L-proline L-arginine salt (2.27 g, yield: 98.7% from dibenzylphosphoryl-L-methionyl-L-prolyl-L-proline methylester). This product gave a single spot respectively having a Rf =0.8 for peptides in the free form and an Rf =0.25 for arginine by thin layer chromatography (developing solvent, n-butanol:acetic acid:water=2:1:1, Colour forming method, spraying of 25% hydrobromic acid and 0.1 ninhydrin, and heating). After hydrolysis of the product with 6N hydrochloric acid, the amino acids were analyzed. Methionine:Proline:Arginine=1.00:2.03:0.95.

Workup

  1. temperatureunder cooling
  2. washthe solution was washed with diethyl ether
  3. additionEthyl acetate (200 ml) was added
  4. stirringwhile stirring strongly
  5. customThe ethyl acetate phase was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a0ff6a8787c54a27912daac040d1f212
Source dataset
uspto-grants-1984_09
Patent number
US04472381

Reaction notes

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