Imidazole → HCID 56777215, compound

HRID 919018Notes

Reaction equation

HRID 919018 reaction equation
N1C=CN=C1.[OH:6][CH2:7][C@@H:8]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10].[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C=O)C>[CH3:12][N:11]([C:9](=[O:10])[C@H:8]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:7][O:6][Si:26]([CH3:28])([CH3:27])[C:29]([CH3:32])([CH3:31])[CH3:30])[O:13][CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 59531201HCID 59531201, compound

Product 1

HCID 56777215HCID 56777215, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (1.8 g, 26.5 mmol) was added to a solution of (R)-benzyl 3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (3 g, 10.6 mmol) in DMF (dimethyl formamide, 15 mL) followed by TBDMSiCl (tert-butyldimethylsilyl chloride, 2.4 g, 15.95 mmol). The reaction stirred for 12 hrs at room temperature under nitrogen atmosphere and was quenched with aqueous ammonium chloride (100 ml). The aqueous layer was extracted with methylene chloride (200 mL) and ethyl acetate (100 mL) and the organic layers were washed with brine and concentrated. The crude product was purified by column chromatography using 10% EtOAc (ethylacetate)-hexanes to give an oil (3 g, 74% yield). 1H NMR (400 MHz, CDCl3) δ═O (s, 6H), 0.9 (s, 9H), 3.2 (s, 3H), 3.8 (s, 3H), 3.8-3.9 (m, 2H), 4.8 (broad s, 1H), 5.1 (q, 2H), 5.7 (d, 1H), 7.2-7.4 (m, 5H).

Workup

  1. customwas quenched with aqueous ammonium chloride (100 ml)
  2. extractionThe aqueous layer was extracted with methylene chloride (200 mL) and ethyl acetate (100 mL)
  3. washthe organic layers were washed with brine
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6518817b58b644fb80b37893a4e1d8a2
Source dataset
uspto-grants-2016_03
Patent number
US09272996B2

Reaction notes

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