Methanol → HCID 118040555, compound

HRID 1050732Notes

Reaction equation

HRID 1050732 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32]C)[CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([C:20]([O:22][CH3:23])=[O:21])[CH:13]=[CH:12][C:11]1=2)C.B(Br)(Br)Br.CO>ClCCl>[OH:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][CH2:24][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH3:1])=[O:34])[CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([C:20]([O:22][CH3:23])=[O:21])[CH:13]=[CH:12][C:11]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 118179066HCID 118179066, compound

Product 1

HCID 118040555HCID 118040555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under argon, 653 mg (1.4 mmol) of the compound from Example 2A were dissolved in 12 ml of dichloromethane and the mixture was cooled to 0° C. 4.6 ml (4.6 mmol) of a 1 M solution of boron tribromide in dichloromethane were slowly added dropwise and the mixture was stirred at 0° C. for another 4 h (clear yellow solution). 7 ml of abs. methanol were then added and the mixture was heated under reflux overnight. The mixture was then concentrated to dryness under reduced pressure and the residue was partitioned between ethyl acetate and 10% strength aqueous sodium carbonate solution. The aqueous phase was re-extracted with ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulphate. After concentration, the residue (519 mg of a brown oil) was purified by column chromatography on silica gel (mobile phase: gradient isohexane/4-32% ethyl acetate).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe mixture was then concentrated to dryness under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and 10% strength aqueous sodium carbonate solution
  5. extractionThe aqueous phase was re-extracted with ethyl acetate
  6. washthe combined organic phases were washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationAfter concentration
  9. customthe residue (519 mg of a brown oil) was purified by column chromatography on silica gel (mobile phase: gradient isohexane/4-32% ethyl acetate)

Sources & evidence

ORD record
ord-0327e49fc0324e2fa134814433fc966d
Source dataset
uspto-grants-2016_07
Patent number
US09387203B2

Reaction notes

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