Hydrogen Bromide → HCID 44596873, compound

HRID 553558Notes

Reaction equation

HRID 553558 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Br:17])[C:14]=1[O:15][CH3:16])[CH2:5][C@:6]([CH3:11])([C:8]([OH:10])=[O:9])[NH2:7].F[C:19](F)(F)C(O)=O.Br.C=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([Br:17])[C:14]=1[O:15][CH3:16])[CH2:19][NH:7][C@@:6]([CH3:11])([C:8]([OH:10])=[O:9])[CH2:5]2

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 44596872HCID 44596872, compound

Product 1

HCID 44596873HCID 44596873, compound

Conditions

Temperature
75 °C

Procedure

Compound 2.5 (4.8 mmol) was added to trifluoroacetic acid (5 mL). HBr (33% in acetic acid, 0.9 mL, 4.8 mmol) was added dropwise to the reaction mixture under nitrogen atmosphere. Upon the addition of the acid, formaldehyde (8.64 mmol, 260 mg, 0.7 mL) was added dropwise and the mixture stirred at 70-80° C. for 17 h. The reaction mixture was cooled, dried and concentrated. APCI MS 378 (M+1). The product was used in the next step.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was cooled
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3bc0f160ad2141fb94b9299b621d244f
Source dataset
uspto-grants-2011_11
Patent number
US08048895B2

Reaction notes

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