Potassium Iodide → Methyl 2-(3-tert-Butoxycarbonylaminopropoxy)-4-tert-butylbenzoate

HRID 644289Notes

Reaction equation

HRID 644289 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:16]([NH:23][CH2:24][CH2:25][CH2:26]Br)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[I-].[K+]>CN(C=O)C>[C:19]([O:18][C:16]([NH:23][CH2:24][CH2:25][CH2:26][O:15][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 20777194Methyl 4-tert-butyl-2-hydroxybenzoate

Product 1

HCID 68530190Methyl 2-(3-tert-Butoxycarbonylaminopropoxy)-4-tert-butylbenzoateYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Methyl 4-tert-butyl-2-hydroxybenzoate (2.41 g, 11.6 mmol) was dissolved in DMF (15 mL) and K2 CO3 (2.39 g, 17.4 mmol) and N-Boc-3-bromopropylamine (4.14 g, 17.4 mmol) was added using DMF (10 mL) to aid the transfer. Potassium iodide (0.30 g) was added, and the reaction stirred at room temperature under nitrogen for 18 hr. The DMF was removed in vacuo and the residue taken up in ethyl acetate and washed with water and brine, dried, and the solvent removed in vacuo to give a viscous brown oil. Purification by chromaotgraphy over silica on a preparative scale apparatus, eluting with a gradient of hexane to hexane:ethyl acetate (70:30) gave 1.91 g (45.2%) of a viscous yellow oil.

Workup

  1. customThe DMF was removed in vacuo
  2. washwashed with water and brine
  3. customdried
  4. customthe solvent removed in vacuo
  5. customto give a viscous brown oil
  6. customPurification by chromaotgraphy over silica on a preparative scale apparatus
  7. washeluting with a gradient of hexane to hexane:ethyl acetate (70:30)

Sources & evidence

ORD record
ord-77670657196546109d8e761506ef5c33
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

Loading…