Sodium Bicarbonate → HCID 178512908, compound

HRID 413460Notes

Reaction equation

HRID 413460 reaction equation
[NH:1]1[C:42](=[O:43])[C@H:36]([CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])[NH:35][C:33](=[O:34])[C@@H:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:24][C:22](=[O:23])[C@H:17]([CH2:18][C:19](=[O:21])[OH:20])[NH:16][C:14](=[O:15])[CH2:13][NH:12][C:10](=[O:11])[C@@H:2]1[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].C([O-])(O)=[O:45].[Na+]>C1COCC1>[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:42]([OH:45])=[O:43])[CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])=[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]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178512833HCID 178512833, compound

Product 1

HCID 178512908HCID 178512908, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6 g of BOC-Aha-N-succinimidyl ester are added to a solution of 3.05 g of cyclo-(Arg-Gly-Asp-D-Phe-Lys)(SEQ ID NO: 176) in 40 ml of 5% aqueous NaHCO3 and 40 ml of THF. The mixture is stirred for 4 hours and worked-up in the customary manner, affording cyclo-(Arg-Gly-Asp-D-Phe-Lys (BOC-Aha))(SEQ ID NO: 13); RT [C] 27.7; FAB 817. After the BOC group has been eliminated in HCl/dioxane, cyclo-(Arg-Gly-Asp-D-Phe-Lys(Nε-Aha)(SEQ ID NO: 14)×2 TFA; RT [C] 14.76; FAB 717 is obtained after the customary working-up. Cyclo-(Arg-Gly-Asp-D-Phe-Lys(Nε-FCA-Aha))(SEQ ID NO: 15)×TFA; RT [B] 23.8; FAB 1075 is obtained, in analogy with Example 1, by subsequent reaction with FCA-N-succinimidyl ester.

Sources & evidence

ORD record
ord-9b47c9cfcfb7496dacde966055beee66
Source dataset
uspto-grants-2003_05
Patent number
US06566491B2

Reaction notes

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