Sodium Chloride → HCID 68181075, compound

HRID 1746375Notes

Reaction equation

HRID 1746375 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C@@H:8]([CH2:22][CH:23]1[C:28](=[O:29])[O:27][C:26]([CH3:31])([CH3:30])[O:25][C:24]1=[O:32])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C:34]([O-])([O-])=O.[K+].[K+].CI.[Na+].[Cl-]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:33])[NH:7][C@@H:8]([CH2:22][C:23]1([CH3:34])[C:28](=[O:29])[O:27][C:26]([CH3:31])([CH3:30])[O:25][C:24]1=[O:32])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67969538HCID 67969538, compound

Product 1

HCID 68181075HCID 68181075, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

[(S)-2-Biphenyl-4-yl-1-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-ethyl]carbamic acid t-butyl ester (5.0 g, 11 mmol) and K2CO3 (1.8 g, 13.2 mmol) were dissolved in DMF (33.9 mL) and cooled to 0° C. with stirring under nitrogen. Methyl iodide (892 μL) was added and the resulting mixture was stirred at 0° C. for 1 hour. The mixture was allowed to warm to room temperature. Saturated aqueous NaCl (35 mL) and EtOAc (35 mL) were added, and the resulting mixture was stirred for 2 minutes. The layers were separated and the organic layer was evaporated. The residue was triturated with EtOAc (20 mL). The solid was filtered off and dried under vacuum. The filtrate was concentrated and triturated again with EtOAc to yield the title compound (3.9 g).

Workup

  1. stirringthe resulting mixture was stirred at 0° C. for 1 hour
  2. temperatureto warm to room temperature
  3. stirringthe resulting mixture was stirred for 2 minutes
  4. customThe layers were separated
  5. customthe organic layer was evaporated
  6. customThe residue was triturated with EtOAc (20 mL)
  7. filtrationThe solid was filtered off
  8. customdried under vacuum
  9. concentrationThe filtrate was concentrated
  10. customtriturated again with EtOAc

Sources & evidence

ORD record
ord-a73496059e8f4b60867aa59f5955ae47
Source dataset
uspto-grants-2015_10
Patent number
US09150500B2

Reaction notes

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