Methanol → HCID 20058528, compound

HRID 2050566Notes

Reaction equation

HRID 2050566 reaction equation
Cl.Cl.C[O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][CH:19]([OH:31])[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:8]=[CH:9][C:10]=1[O:11]C.C(N(CC)CC)C.B(Br)(Br)[Br:40].CO>ClCCl>[BrH:40].[BrH:40].[OH:31][CH:19]([CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13][C:7]1[CH:6]=[C:5]([OH:4])[C:10]([OH:11])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 25134Boron tribromideHCID 20058478HCID 20058478, compound

Product 1

HCID 20058528HCID 20058528, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The dihydrochloride from step (c) (2.2 g) in dry dichloromethane (100 ml) was treated with triethylamine (1.3 ml, 0.94 g) and stirred under nitrogen for 15 minutes. The resulting suspension was cooled to -70°, boron tribromide (2.2 ml, 5.85 g) added and the mixture allowed to warm to ambient temperature with stirring over 18 hours. Methanol (10 ml) was added, the resulting solution evaporated to dryness and the solid residue recrystallised from 2-propanol giving the title compound (2.2 g), as the dihydrobromide salt, colorless needles mp 137°-139°.

Workup

  1. temperatureThe resulting suspension was cooled to -70°
  2. stirringwith stirring over 18 hours
  3. customthe resulting solution evaporated to dryness
  4. customthe solid residue recrystallised from 2-propanol giving the title compound (2.2 g)

Sources & evidence

ORD record
ord-591110a501314103a35d205abf6a1531
Source dataset
uspto-grants-1991_05
Patent number
US05013760

Reaction notes

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