Aminoglutethimide → HCID 178465153, compound

HRID 1757377Notes

Reaction equation

HRID 1757377 reaction equation
[CH3:1][CH2:2][NH:3][C:4]([C@H:6]1[N:10]([C:11]([C@@H:13]([NH:21][C:22]([C@@H:24]([NH:29][C:30]([C@H:32]([NH:37][C:38]([C@@H:40]([NH:49][C:50]([C@@H:52]([NH:55][C:56]([C@@H:58]([NH:69][C:70]([C@@H:72]([NH:79][C:80]([C@H:82]2[NH:87][C:85](=[O:86])[CH2:84][CH2:83]2)=[O:81])[CH2:73][C:74]2[N:78]=[CH:77][NH:76][CH:75]=2)=[O:71])[CH2:59][C:60]2[C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][C:63]=3[NH:62][CH:61]=2)=[O:57])[CH2:53][OH:54])=[O:51])[CH2:41][C:42]2[CH:43]=[CH:44][C:45]([OH:48])=[CH:46][CH:47]=2)=[O:39])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:31])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:23])[CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH2:20])=[NH:19])=[O:12])[CH2:9][CH2:8][CH2:7]1)=[O:5].CC(O)=O.CCC1(C2C=CC(N)=CC=2)C(=O)NC(=O)CC1.[OH-].[Na+]>CO>[CH3:1][CH2:2][NH:3][C:4]([C@H:6]1[N:10]([C:11]([C@@H:13]([NH:21][C:22]([C@@H:24]([NH:29][C:30]([C@H:32]([NH:37][C:38]([C@@H:40]([NH:49][C:50]([C@@H:52]([NH:55][C:56]([C@@H:58]([NH:69][C:70]([C@@H:72]([NH:79][C:80]([C@H:82]2[NH:87][C:85](=[O:86])[CH2:84][CH2:83]2)=[O:81])[CH2:73][C:74]2[N:78]=[CH:77][NH:76][CH:75]=2)=[O:71])[CH2:59][C:60]2[C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][C:63]=3[NH:62][CH:61]=2)=[O:57])[CH2:53][OH:54])=[O:51])[CH2:41][C:42]2[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=2)=[O:39])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:31])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:23])[CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH2:20])=[NH:19])=[O:12])[CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 2145AminoglutethimideHCID 14798Sodium HydroxideHCID 178476396HCID 178476396, compound

Product 1

HCID 178465153HCID 178465153, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1 gram of leuprolide acetate in 15 ml of methanol was loaded onto an anion exchange resin in the hydroxide ion form (Bio-Rad AG-1×2, 200-400 mesh, Bio-Rad Laboratories, 237-T Putnam Ave., Cambridge, Mass. 02139). The resin column had been prepared by passing a solution of 0.5M methanolic sodium hydroxide through a column of the resinin chloride ion form, as obtained from the manufacturer. The free base formof leuprolide was eluted from the column with methanol and the solvent removed by evaporation to yield leuprolide in the free base form. HPLC determination of the putiry of the eluted material indicated that it was 96.5% pure.

Workup

  1. customThe resin column had been prepared
  2. customas obtained from the manufacturer
  3. washThe free base formof leuprolide was eluted from the column with methanol
  4. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-b27af02bbc43472fa1825e4b788758a5
Source dataset
uspto-grants-1995_08
Patent number
US05446025

Reaction notes

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