Methanol → HCID 45139978, compound

HRID 574301Notes

Reaction equation

HRID 574301 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 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

Compound 38a (3.21 g, 9.70 mmol) was dissolved in 120 ml of CH2Cl2 and cooled to −78° C. 1M boron tribromide (30 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 (Na2SO4), filtered, and concentrated to yield the crude product. Column chromatography (7:3:1 CH2Cl2:MeOH:Et3N) afforded 2.41 g (84%) of 39a. 1H NMR (400 MHz, CDCl3) 0.98-1.02 (t, 3H, 7.6 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, 9H), 6.45 (s, 1H), 6.53-6.55 (d, 1H, J=9.2 Hz), 6.84-6.85 (d, 1H, J=8.4 Hz).

Workup

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

Sources & evidence

ORD record
ord-d672c7fe1140407c8781909f3b6eb523
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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