Methanol → HCID 20670018, compound

HRID 1532312Notes

Reaction equation

HRID 1532312 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[S:11][C:12]1[C:17]([C:18]([NH:20][CH2:21][C:22]23[CH2:31][CH:26]4[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]4)[CH2:23]2)[CH2:29]3)=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1.B(Br)(Br)Br.CO>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[S:11][C:12]1[C:17]([C:18]([NH:20][CH2:21][C:22]23[CH2:31][CH:26]4[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]4)[CH2:23]2)[CH2:29]3)=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 20670019HCID 20670019, compound

Product 1

HCID 20670018HCID 20670018, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the dimethoxy compound from Example 37 (1.0 g) in dichloromethane (20 ml) at −78° C., was added boron tribromide (5.5 ml of a 1M solution in dichloromethane. The reaction mixture was stirred for 24 hours, warming to ambient temperature. Methanol (5 ml) was added and the solvent was removed under reduced pressure and the residue purified by silica gel chromatography eluting with dichloromethane, ethyl acetate, acetic acid (4:1:0.1). The fractions containing product were combined and the solvent removed under reduced pressure to give the title compound as a white solid (0.40 g).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue purified by silica gel chromatography
  3. washeluting with dichloromethane, ethyl acetate, acetic acid (4:1:0.1)
  4. additionThe fractions containing product
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e45db67d36ec4e5883dd76ef42b95b3a
Source dataset
uspto-grants-2001_03
Patent number
US06201024B1

Reaction notes

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