Cesium carbonate → 3-(2-tert-Butoxycarbonylamino-ethoxy)-4-cyano-benzoic acid methyl ester

HRID 1585909Notes

Reaction equation

HRID 1585909 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9]Br)([CH3:4])([CH3:3])[CH3:2].[C:12]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[OH:24])#[N:13].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([C:12]#[N:13])=[C:15]([O:24][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:11])[CH:16]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 16641129Methyl 4-cyano-3-hydroxybenzoate

Product 1

HCID 540915033-(2-tert-Butoxycarbonylamino-ethoxy)-4-cyano-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Bromoethyl)carbamic acid tert-butyl ester (700 mg, 3.12 mmol) from step 1 and 4-cyano-3-hydroxybenzoic acid methyl ester (Example 34 Step 3, 550 mg, 3.12 mmol) was dissolved in DMF (4.5 ml). Cs2CO3 (2.03 g, 6.24 mmol) was added and the reaction stirred at room temperature for 2 hours. The reaction mixture was filtered through celite and washed with DMF (3×10 mL). The DMF was removed in vacuo. The residue was purified by flash chromatography (12% EtOAc/Hexane) to yield the desired product.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with DMF (3×10 mL)
  3. customThe DMF was removed in vacuo
  4. customThe residue was purified by flash chromatography (12% EtOAc/Hexane)

Sources & evidence

ORD record
ord-f89fbb0ad19a49359fd177b4640d0f7e
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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