Water → HCID 178512819, compound

HRID 1751165Notes

Reaction equation

HRID 1751165 reaction equation
[NH2:1][C@H:2]([C:11]([NH:13][CH2:14][C:15]([NH:17][C@H:18]([C:23]([NH:25][C@H:26]([C:37]([N:39]1[CH2:52][CH2:51][CH2:50][C@H:40]1[C:41]([NH:43][C@H:44]([C:47]([NH2:49])=[O:48])[CH2:45][SH:46])=[O:42])=[O:38])[CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=[O:24])[CH2:19][C:20](=[O:22])[OH:21])=[O:16])=[O:12])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:10])[NH2:9].[OH2:53].[OH-].[NH4+].O=O>C(#N)C>[CH:34]1[CH:33]=[CH:32][C:31]2[NH:30][CH:29]=[C:28]([CH2:27][C@@H:26]3[NH:25][C:23](=[O:24])[C@H:18]([CH2:19][C:20]([OH:21])=[O:22])[NH:17][C:15](=[O:16])[CH2:14][NH:13][C:11](=[O:12])[C@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH2:9])=[NH:10])[NH:1][C:47](=[O:53])[CH2:44][CH2:45][S:46][S:46][CH2:45][C@@H:44]([C:47]([NH2:49])=[O:48])[NH:43][C:41](=[O:42])[C@H:40]4[N:39]([CH2:52][CH2:51][CH2:50]4)[C:37]3=[O:38])[C:36]=2[CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 977OxygenHCID 14923Ammonium HydroxideHCID 178512821HCID 178512821, compound

Product 1

HCID 178512819HCID 178512819, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Mpa-Har-Gly-Asp-Trp-Pro-Cys-NH2 (60 gm; obtained from Ex-19) was charged in to a stirred solution of water (6 L) and acetonitrile (6 L) at 25° C.-35° C. Adjusted the pH of the solution to 8-8.5 with 2% ammonium hydroxide solution (500 ml). Passed oxygen gas in to the reaction mass for about 10 to 12 hrs under pH of about 8.5-about 8.8. Adjusted pH of the reaction mass to about 5 to about 6 with 1% acetic acid 100 ml) and concentrated the reaction solution at 30° C. to 35° C. under high vacuum till 30% of the solution remains in the reaction vessel and then lyophilized the reaction solution to obtain the title compound.

Workup

  1. customobtained from Ex-19)
  2. concentrationAdjusted pH of the reaction mass to about 5 to about 6 with 1% acetic acid 100 ml) and concentrated the reaction solution at 30° C. to 35° C. under high vacuum till 30% of the solution

Sources & evidence

ORD record
ord-a83bf29430e549ac83d1084a6805dfc5
Source dataset
uspto-grants-2015_10
Patent number
US09156885B2

Reaction notes

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