Sodium Hydroxide → HCID 178448339, compound

HRID 1290595Notes

Reaction equation

HRID 1290595 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

Procedure

Two grams (g) of BOC-Gly-D-Arg-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 2N sodium hydroxide solution to form an admixture. The admixture was then stirred for 3 hours at 20 degress 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 Na2 So4, evaporated again and the resultant BOC-Gly-D-Arg-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-D-Arg-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. customAfter evaporation
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried over Na2 So4
  5. customevaporated again
  6. stirringthe resultant BOC-Gly-D-Arg-Gly-Asp-Phe-Val-OH (SEQ ID NO 2) was stirred at 20 C
  7. waitfor 2 hours with 20 ml of 2 N HCl in dioxane
  8. customThe resultant admixture was evaporated

Sources & evidence

ORD record
ord-d2ca7167a327450eb5974839b787cd89
Source dataset
uspto-grants-1998_05
Patent number
US05753230

Reaction notes

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