Cesium carbonate → HCID 89726688, compound

HRID 1777759Notes

Reaction equation

HRID 1777759 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([CH3:15])[CH2:8][C:9]1[N:13]=[C:12]([CH3:14])[NH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>CC#N>[C:1]([O:5][C:6]([N:7]([CH2:8][C:9]1[N:13]=[C:12]([CH3:14])[N:11]([CH2:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[N:10]=1)[CH3:15])=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 64511196HCID 64511196, compound

Product 1

HCID 89726688HCID 89726688, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl-(5-methyl-1H-[1,2,4]triazol-3-ylmethyl)-carbamic acid tert-butyl ester (470 mg) in MeCN (20 mL) was added Cs2CO3 (677 mg) followed by benzyl bromoacetate (0.343 mL). The reaction mixture was stirred at RT overnight and evaporated to dryness. The residue was taken up in DCM and washed with water. The aq. layers were extracted with DCM, the combined org. layers were dried (Na2SO4), filtered off and evaporated in vacuo. The residue was purified by CC (silica gel, Hept/EA 1/1 then DCM/MeOH 9/1) to afford benzyl 2-(3-(((tert-butoxycarbonyl)(methyl)amino)methyl)-5-methyl-1H-1,2,4-triazol-1-yl)acetate (290 mg, yellow oil). LC-MS (B): tR=0.83 min; [M+H]+: 375.14. 1H-NMR (CD3OD): 7.39-7.35 (m, 5H); 5.24 (s, 2H); 5.09 (s, 2H); 4.43 (m, 2H); 2.89 (m, 3H); 2.41 (s, 3H); 1.44 (d, 9H). Roesy signal seen between CH2 at 5.09 ppm and CH3 at 2.41 ppm.

Workup

  1. customevaporated to dryness
  2. washwashed with water
  3. extractionThe aq. layers were extracted with DCM
  4. dry with materiallayers were dried (Na2SO4)
  5. filtrationfiltered off
  6. customevaporated in vacuo
  7. customThe residue was purified by CC (silica gel

Sources & evidence

ORD record
ord-4e63248db40c4fadbddcf8afbabb52fc
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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