HCID 59571192, compound → HCID 59571194, compound

HRID 389216Notes

Reaction equation

HRID 389216 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18](=[O:35])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26])[C@H:15]([C:36]([O:38]CC)=[O:37])[CH2:14]2)=[CH:4][C:3]=1[O:41][CH3:42]>C1COCC1.CCO.[Li+].[OH-].OS([O-])(=O)=O.[K+]>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18](=[O:35])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26])[C@H:15]([C:36]([OH:38])=[O:37])[CH2:14]2)=[CH:4][C:3]=1[O:41][CH3:42]

Participants

6

Reactant 1

HCID 59571192HCID 59571192, compound

Product 1

HCID 59571194HCID 59571194, compoundYield 96.1%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolventHCID 516920Potassium bisulfateSolvent

Procedure

A solution of the product from Step 1 (400 mg, 0.617 mmol) in THF (5 mL), EtOH (1 mL) and 1N aqueous LiOH (4.32 mL) was stirred at RT for 2 hours. The reaction solution was diluted with 10% KHSO4 (20 mL) and extracted with ether (3×70 mL). The combined ether layers were washed with water (50 mL), brine (30 mL), dried over Na2SO4, filtered and concentrated to give the title product (368 mg). LRMS (ESI) m/z 620.4 [(M+H)+; calcd for C29H39BrN3O7: 620.2].

Workup

  1. extractionextracted with ether (3×70 mL)
  2. washThe combined ether layers were washed with water (50 mL), brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-973fe61cb05947b9a33d860278c549df
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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