Methanol → HCID 45139978, compound

HRID 574282Notes

Reaction equation

HRID 574282 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:14][CH2:15][CH3:16])[CH2:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+].CO>C(Cl)Cl.CCN(CC)CC>[N:19]1([CH2:18][CH2:17][N:13]([CH2:14][CH2:15][CH3:16])[CH:9]2[CH2:10][C:11]3[CH:12]=[C:3]([OH:2])[CH:4]=[CH:5][C:6]=3[CH2:7][CH2:8]2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 45139977HCID 45139977, compound

Product 1

HCID 45139978HCID 45139978, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

Compound 8a (2.23 g, 6.73 mmol) was dissolved in 80 ml of CH2Cl2 and cooled to −78° C. 1M boron tribromide solution in dichloromethane (20 ml) was added dropwise and the mixture was allowed to warm to ambient temperature and was stirred overnight. Sat. NaHCO3 was added and the product extracted with dichloromethane, dried over Na2SO4, filtered, and concentrated to yield the crude product. Column chromatography (7:2:1; CH2Cl2:MeOH:Et3N) afforded 1.62 g (76%) of 9a as brown wax. 1H NMR (400 MHz, CDCl3) δ ppm 0.84-0.87 (t, 3H, J=6 Hz), 1.27-1.31 (m, 2H), 1.70-1.82 (m, 3H), 2.25-2.28 (m, 1H), 2.58-2.06 (m, 1H), 2.73-2.78 (m, 4H), 2.97-3.09 (m, 5H), 3.16-3.20 (m, 7H), 6.45 (s, 1H), 6.53-6.55 (d, 1H, J=9.2 Hz), 6.84-6.86 (d, 1H, J=8 Hz).

Workup

  1. temperatureto warm to ambient temperature
  2. extractionthe product extracted with dichloromethane
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield the crude product

Sources & evidence

ORD record
ord-cc59c93a4bd74156a420411004b7cc0f
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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