Butyl bromide → HCID 75631375, compound

HRID 1911229Notes

Reaction equation

HRID 1911229 reaction equation
Cl.[F:2][CH:3]([F:12])[C@H:4]1[CH2:9][NH:8][CH2:7][C@@H:6]([OH:10])[C@@H:5]1[OH:11].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH3:22]>CN(C=O)C>[CH2:19]([N:8]1[CH2:9][CH:4]([CH:3]([F:2])[F:12])[CH:5]([OH:11])[CH:6]([OH:10])[CH2:7]1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 67100005HCID 67100005, compound

Product 1

HCID 75631375HCID 75631375, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6 (0.30 g, 1.4 mmol), K2CO3 (0.48 g, 3.5 mmol) and BuBr (0.20 g, 1.4 mmol) was combined in DMF (10 mL) and heated overnight at 60° C. The solvent was evaporated in vacuo and the residue was dissolved in EtOAc, washed with water and then brine and dried over Na2SO4. After filtration, the filtrate was evaporated in vacuo to give the crude product which was purified by chromatography (CH2Cl2/(9:1) MeOH/NH4OH) to give the title compound (0.25 g, 80%) as a colorless syrup. MH+=224. 1H NMR (DMSO-d6) 6.2 (t, 1H, J=57 Hz), 5.13 (d, 1H, ex), 4.91 (d, 1H, ex), 3.3 (m, 1H), 3.1 (m, 1H), 2.9 (m, 2H), 2.3 (m, 2H), 1.95 (m, 2H), 1.75 (t, 1H), 1.2-1.5 (2m, 4H), 0.9 (t, 3H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialbrine and dried over Na2SO4
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated in vacuo
  7. customto give the crude product which
  8. customwas purified by chromatography (CH2Cl2/(9:1) MeOH/NH4OH)

Sources & evidence

ORD record
ord-24acd6af69024228a9224c1d5f7131ed
Source dataset
uspto-grants-2013_12
Patent number
US08604057B2

Reaction notes

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