Butyl bromide → HCID 75631375, compound

HRID 1479710Notes

Reaction equation

HRID 1479710 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 sirup. 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-7895ec5ef7024ae78cc8bcb81447c579
Source dataset
uspto-grants-2016_08
Patent number
US09409862B2

Reaction notes

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