Sodium Hydroxide → HCID 178448341, compound

HRID 361306Notes

Reaction equation

HRID 361306 reaction equation
[NH:1]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[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]([NH:42][C@H:43]([C:45]([O:47]C)=[O:46])[CH3:44])=[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>[NH:1]([C:49]([O:51][C:52]([CH3:55])([CH3:53])[CH3:54])=[O:50])[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]([NH:42][C@H:43]([C:45]([OH:47])=[O:46])[CH3:44])=[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 178501485HCID 178501485, compound

Product 1

HCID 178448341HCID 178448341, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.0 g of BOC-Arg-Gly-Asp-D-Phe-Val-Ala-OMe are dissolved in 60 ml of methanol, 1.5 ml of 2N sodium hydoxide solution are added and the mixture is stirred for 3 hours at 20°. After evaporation the residue is taken up in water, acidified to pH 3 with dilute HCl and extracted with ethyl acetate. The extract is dried over Na2SO4, evaporated again and the BOC-Arg-Gly-Asp-D-Phe-Val-Ala-OH obtained is stirred at 20° for 2 hours with 20 ml of 2N HCl in dioxane. The mixture is evaporated, the H-Arg-Gly-Asp-D-Phe-Val-Ala-OH obtained is dissolved in a mixture of 1800 ml of dichloromethane and 200 ml of DMF and cooled to 0°, 0.5 g of DCCI, 0.3 g of HOBt and 0.23 ml of N-methylmorpholine are added successively with stirring, and the mixture is stirred for a further 24 hours at 0° and 48 hours at 20°. The solution is concentrated and tested with a mixed bed ion exchange to free it from salts. This is then filtered off, the solution is evaporated and the residue is purified by chromatography. Cyclo(-Arg-Gly-Asp-D-Phe-Val-Ala) M+ : 646 FAB is obtained;

Workup

  1. customAfter evaporation the residue
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract is dried over Na2SO4
  4. customevaporated again

Sources & evidence

ORD record
ord-42345146d5734fa4a4be2606d1bdf42d
Source dataset
uspto-grants-1999_02
Patent number
US05866540

Reaction notes

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