HCID 131725208, compound → HCID 69139506, compound

HRID 1062713Notes

Reaction equation

HRID 1062713 reaction equation
[ClH:1].[CH3:2][C:3]1([CH3:50])[C:7](=[O:8])[N:6]([C@@H:9]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:10][NH:11][C@H:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][C:14]([O:16]CC)=[O:15])[C:5](=[O:29])[N:4]1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38]([NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[CH3:47])=[O:39])=[C:33]([O:48][CH3:49])[CH:32]=1>Cl.C1COCC1>[ClH:1].[CH3:50][C:3]1([CH3:2])[C:7](=[O:8])[N:6]([C@@H:9]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:10][NH:11][C@H:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:13][C:14]([OH:16])=[O:15])[C:5](=[O:29])[N:4]1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38]([NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[CH3:47])=[O:39])=[C:33]([O:48][CH3:49])[CH:32]=1

Participants

4

Reactant 1

HCID 131725208HCID 131725208, compound

Product 1

HCID 69139506HCID 69139506, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 100 mg (0.149 mmol) of the compound of example 9 in 6N hydrochloric acid and THF was heated at 60° C. for 4 h. The THF was removed in vacuo and the residue was freeze-dried. Following purification by means of preparative HPLC, chromatography over silica gel using dichloromethane/methanol/acetic acid/water (9.5/0.5/0.05/0.05), concentrating the product fractions and freeze-drying in the presence of 2N hydrochloric acid, 20 mg (21%) of the title compound were obtained.

Workup

  1. customThe THF was removed in vacuo
  2. customthe residue was freeze-dried
  3. custompurification by means of preparative HPLC, chromatography over silica gel
  4. concentrationconcentrating the product fractions
  5. dry with materialfreeze-drying in the presence of 2N hydrochloric acid

Sources & evidence

ORD record
ord-4d225b121f24413c82a306cf31e3ff46
Source dataset
uspto-grants-2005_11
Patent number
US06962937B2

Reaction notes

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