Ethyl Acetate → HCID 11259118, compound

HRID 1434957Notes

Reaction equation

HRID 1434957 reaction equation
CO[N:3]=[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]4[CH2:29][C:28]([CH3:31])([CH3:30])[NH:27][C:26]([CH3:33])([CH3:32])[CH2:25]4)[N:18]=3)=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)[CH3:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].S([O-])([O-])(=O)=O.[Na+].[Na+].CCOC(C)=O>C1COCC1>[NH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]4[CH2:29][C:28]([CH3:31])([CH3:30])[NH:27][C:26]([CH3:32])([CH3:33])[CH2:25]4)[N:18]=3)=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)[CH3:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 72822011HCID 72822011, compound

Product 1

HCID 11259118HCID 11259118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Compound of Example 51 (366 mg, 0.79 mmol) was dissolved in 20 ml THF and 0.35 ml of LAH (˜2.3 M suspension in THF) added dropwise at room temperature. Afterwards this mixture was stirred for 2 hours at 60° C. After cooling to room temperature 40 ml of saturated sodium sulfate solution was added and stirred for 15 minutes. The title compound was isolated by extraction with EtOAc and purified by chromatography on silicagel (DCM/MeOH/ammonia:95/5/0.5). Yield: 160 mg (47%).

Workup

  1. additionwas added
  2. stirringstirred for 15 minutes

Sources & evidence

ORD record
ord-de3c6c9c16d24722983d789c0455a094
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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