Triethylamine → HCID 11125254, compound

HRID 891007Notes

Reaction equation

HRID 891007 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[N:24]1[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[C:26]([C:33]2[C:37](=[O:38])[N:36]([CH3:39])[C:35](=[O:40])[C:34]=2[C:41]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:43](C(OC(C)(C)C)=O)[CH:42]=2)=[CH:25]1)(=[O:3])[CH3:2].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(O)=O>[NH:43]1[C:44]2[C:49](=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:41]([C:34]2[C:35](=[O:40])[N:36]([CH3:39])[C:37](=[O:38])[C:33]=2[C:26]2[C:27]3[C:28](=[N:29][CH:30]=[CH:31][CH:32]=3)[N:24]([C@@H:6]3[O:7][C@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:5]3[O:4][C:1](=[O:3])[CH3:2])[CH:25]=2)=[CH:42]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 11083249HCID 11083249, compound

Product 1

HCID 11125254HCID 11125254, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The compound of Example 16a (0.114 mmol) is dissolved in 20 ml of formic acid. After stirring for 24 hours at ambient temperature, the solution is neutralised by adding, dropwise, triethylamine, and then saturated aqueous sodium bicarbonate solution. The mixture is extracted with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution and are then dried over magnesium sulphate and filtered; the solvent is evaporated off. After purification by chromatography on silica gel (cyclohexane/ethyl acetate: 1/1), the expected product is isolated.

Workup

  1. additionby adding
  2. extractionThe mixture is extracted with ethyl acetate
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialare then dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is evaporated off
  7. customAfter purification by chromatography on silica gel (cyclohexane/ethyl acetate: 1/1)

Sources & evidence

ORD record
ord-597ca97f4e934e05bc102550cdca590e
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Reaction notes

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