Imidazole → HCID 68545986, compound

HRID 2388572Notes

Reaction equation

HRID 2388572 reaction equation
[Cl:1][C:2]1[C:3]([CH3:37])=[C:4]([NH:10][C@H:11]([C@@H:34]([OH:36])[CH3:35])[C:12]([NH:14][NH:15][C:16](=[O:33])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].CN(C=O)C.N1C=CN=C1.[C:48]([Si:52](Cl)([CH3:54])[CH3:53])([CH3:51])([CH3:50])[CH3:49]>CCOC(C)=O.O>[Si:52]([O:36][C@@H:34]([CH3:35])[C@@H:11]([NH:10][C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[C:3]=1[CH3:37])[C:12]([NH:14][NH:15][C:16](=[O:33])[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)=[O:13])([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:54])[CH3:53]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 68543906HCID 68543906, compound

Product 1

HCID 68545986HCID 68545986, compoundYield 107.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 100 mL round bottomed flask was charged with N′-((2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)-4-(4-methoxybenzyloxy)benzohydrazide (3.53 g, 6.7 mmol) and DMF (120 mL). Imidazole (1.84 g, 27 mmol) and tert-butyldimethyl silyl chloride (2.52 g, 16.75 mmol) were then added to the mixture which was stirred at room temperature for 17.5 h. Water (60 mL) was added to the mixture followed by EtOAc (100 mL). The phases were partitioned and the organic phase washed with water (70 mL) (×4), brine (50 mL), dried (Na2SO4) and concentrated to furnish a white solid. Purification by flash column chromatography [EtOAc-hexanes (1:1) as eluent] afforded the title compound as a colorless oil (4.58 g, 35% yield). No 1H data available.

Workup

  1. customThe phases were partitioned
  2. washthe organic phase washed with water (70 mL) (×4), brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto furnish a white solid
  6. customPurification by flash column chromatography [EtOAc-hexanes (1:1) as eluent]

Sources & evidence

ORD record
ord-9b3454b40e53482a83c3781bafab103f
Source dataset
uspto-grants-2012_09
Patent number
US08268872B2

Reaction notes

Loading…