Sodium Hydroxide → HCID 178448343, compound

HRID 1827258Notes

Reaction equation

HRID 1827258 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([NH:24][C@@H:25]([C:33]([NH:35][C@H:36]([C:40]([O:42]C)=[O:41])[CH:37]([CH3:39])[CH3:38])=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:23])[CH2:18][C:19](=[O:21])[OH:20])=[O:15])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[OH-].[Na+]>CO>[NH2:1][C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([NH:24][C@@H:25]([C:33]([NH:35][C@H:36]([C:40]([OH:42])=[O:41])[CH:37]([CH3:39])[CH3:38])=[O:34])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:23])[CH2:18][C:19](=[O:20])[OH:21])=[O:15])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501510HCID 178501510, compound

Product 1

HCID 178448343HCID 178448343, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Two grams (g) of BOC-Arg-Gly-Asp-D-Phe-Val-OMe (SEQ ID NO 1) were first dissolved in 60 milliliters (ml) of methanol to which was added 1.5 ml of 2 N sodium hydroxide solution to form an admixture. The admixture was then stirred for 3 hours at 20 degrees C. (20C). After evaporation, the residue was taken up in water and acidified to pH 3 with diluted HCl and extracted with ethyl acetate. The extract was dried over Na2SO4, evaporated again and the resultant BOC-Arg-Gly-Asp-D-Phe-Val-OH (SEQ ID NO 2) was stirred at 20C for 2 hours with 20 ml of 2 N HCl in dioxane. The resultant admixture was evaporated to obtain H-Arg-Gly-Asp-D-Phe-Val-OH (SEQ ID NO 3) that was subsequently dissolved in a mixture of 1800 ml of dichloromethane and 200 ml of dimethylformamide (DMF) followed by cooling to 0C. Thereafter, 0.5 g of dicyclohexylcarbodiimide (DCCI), 0.3 g of 1-hydroxybenzotriazole (HOBt) and 0.23 ml of N-methylmorpholine were added sequentially with stirring.

Workup

  1. customto form an admixture
  2. customAfter evaporation
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over Na2SO4
  5. customevaporated again
  6. stirringthe resultant BOC-Arg-Gly-Asp-D-Phe-Val-OH (SEQ ID NO 2) was stirred at 20C for 2 hours with 20 ml of 2 N HCl in dioxane
  7. customThe resultant admixture was evaporated

Sources & evidence

ORD record
ord-cc737aeae00a44c8b4b15f2ba142ea62
Source dataset
uspto-grants-2006_05
Patent number
US07053041B1

Reaction notes

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