Methanol → HCID 18536258, compound

HRID 412013Notes

Reaction equation

HRID 412013 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:15][CH2:14]2)=[O:9])=[C:6]([O:30]C)[CH:5]=1.B(Br)(Br)Br.CO>ClCCl>[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:15][CH2:14]2)=[O:9])=[C:6]([OH:30])[CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 18536231HCID 18536231, compound

Product 1

HCID 18536258HCID 18536258, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product of step (b) (3 g) in dichloromethane (50 ml) was cooled to −78° C. and a 1.0M solution of boron tribromide in dichloromethane (8.5 ml) added. After 1 hour the solution was allowed to warm to room temperature. After 3 hours, methanol (6 ml) was added and the solution concentrated. This process was repeated, the residue dissolved in methanol, treated with concentrated hydrochloric acid and stirred at room temperature for 3 hours. The solution was concentrated, sodium bicarbonate solution and ethyl acetate were added, the organic phase separated, dried and concentrated to a gum which was purified by chromatography (dichloromethane:methanol, 97:3) to give the product as a solid (2.0 g), m.p. 238-240° C.

Workup

  1. waitAfter 3 hours
  2. concentrationthe solution concentrated
  3. dissolutionthe residue dissolved in methanol
  4. additiontreated with concentrated hydrochloric acid
  5. concentrationThe solution was concentrated
  6. additionsodium bicarbonate solution and ethyl acetate were added
  7. customthe organic phase separated
  8. customdried
  9. concentrationconcentrated to a gum which
  10. customwas purified by chromatography (dichloromethane:methanol, 97:3)

Sources & evidence

ORD record
ord-88908149a36c4c9abad9972ed46d90c8
Source dataset
uspto-grants-2003_05
Patent number
US06562825B1

Reaction notes

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