Sodium Iodide → 2-Methyl-2-propanyl {(1S)-2-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl}-1-[(2S)-2-oxiranyl]ethyl}carbamate

HRID 1815590Notes

Reaction equation

HRID 1815590 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[C:6]([CH3:9])[S:7][CH:8]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C@H:19]2[CH2:21][O:20]2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:9][C:6]1[S:7][CH:8]=[C:4]([CH2:3][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[C@H:19]3[CH2:21][O:20]3)=[CH:13][CH:12]=2)[N:5]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 9993752HCID 9993752, compound

Product 1

HCID 116180512-Methyl-2-propanyl {(1S)-2-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl}-1-[(2S)-2-oxiranyl]ethyl}carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

0.6 g (3.26 mmol) 4-Chloromethyl-2-methyl-thiazole hydrochloride was added to a stirred solution of 0.76 g (2.71 mmol) tert-butyl (1S)-2-(4-hydroxyphenyl)-1-[(2S)-oxiranyl]ethylcarbamate in 15 ml N,N-dimethylformamide. 3.25 g (10 mmol) cesium carbonate and 550 mg (3.66 mmol) sodium iodide was added, and the mixture was stirred at 20° C. for 24 hours. 200 ml ethyl acetate was added, and the mixture was filtered. The filtrate was extracted with water (5×50 ml), and the organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silicagel column using hexane-ethyl acetate (1:1) as solvent to yield 820 mg (Y=78%) title compound. 1H-NMR (CDCl3): δ 1.36 (9H,s), 2.71 (3H,s), 2.75-2.95 (4H,m), 3.61 (1H,s(br)), 4.39 (1H,s(br)), 5.11 (2H,s), 6.91 (2H,d), 7.11 (2H,d), 7.12 (1H,s).

Workup

  1. filtrationthe mixture was filtered
  2. extractionThe filtrate was extracted with water (5×50 ml)
  3. dry with materialthe organic phase was dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on silicagel column

Sources & evidence

ORD record
ord-f8408ccbfeb8423ea199009b2ee765cf
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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