Sodium Hydroxide → HCID 178448339, compound

HRID 902398Notes

Reaction equation

HRID 902398 reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][C@@H:6]([C:14]([NH:16][CH2:17][C:18]([NH:20][C@H:21]([C:26]([NH:28][C@H:29]([C:37]([NH:39][C@H:40]([C:44]([O:46]C)=[O:45])[CH:41]([CH3:43])[CH3:42])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[CH2:22][C:23](=[O:25])[OH:24])=[O:19])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:13])[NH2:12])=[O:4].[OH-].[Na+]>CO>[NH2:1][CH2:2][C:3]([NH:5][C@@H:6]([C:14]([NH:16][CH2:17][C:18]([NH:20][C@H:21]([C:26]([NH:28][C@H:29]([C:37]([NH:39][C@H:40]([C:44]([OH:46])=[O:45])[CH:41]([CH3:43])[CH3:42])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[CH2:22][C:23](=[O:24])[OH:25])=[O:19])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501509HCID 178501509, compound

Product 1

HCID 178448339HCID 178448339, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Two grams (g) of BOC-Gly-DArg-Gly-Asp-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. (20° C.). After evaporation, the residue was taken up in water, acidified to pH 3 with diluted HCl and extracted with ethyl acetate. The extract was dried over Na2SO4, evaporated again and the resultant BOC-Gly-DArg-Gly-Asp-Phe-Val-OH (SEQ ID NO: 2) was stirred at 20° C. for 2 hours with 20 ml of 2 N HCl in dioxane. The resultant admixture was evaporated to obtain H-Gly-DArg-Gly-Asp-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 0° C. Thereafter, 0.5 g of dicyclohexylcarbodiimide (DCCI), 0.3 g of 1-hydroxybenzotriazole (HOBt) and 0.23 ml of N-methylmorpholine were added successively with stirring.

Workup

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

Sources & evidence

ORD record
ord-753c6d3e7a034824b24d4e6452faf715
Source dataset
uspto-grants-2008_04
Patent number
US07365054B2

Reaction notes

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