Water → HCID 178468578, compound

HRID 2068279Notes

Reaction equation

HRID 2068279 reaction equation
[N:1]#[C:2]Br.O.[NH2:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20][CH2:19]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(#N)C.CO>[NH2:1][C:2]1[N:17]([C@H:18]2[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20][CH2:19]2)[C:16]2[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=2[N:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 178469030HCID 178469030, compound

Product 1

HCID 178468578HCID 178468578, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

5.0 M cyanogen bromide in acetonitrile (1.0 mL) was added to water (35 mL) in a 250 mL round-bottom flask at room temperature with stirring. To this was added dropwise via an addition funnel ethyl 3-amino-4-(trans-4-hydroxycyclohexylamino)benzoate (0.91 g, 0.0033 mol) in methanol (70 mL) over 1 hour. After 3 hours the reaction mixture was concentrated to an off white residue. The residue was triturated with ethyl acetate and dried overnight in vacuo to give the title compound (0.97 g, 98%) as an off white solid.

Workup

  1. concentrationAfter 3 hours the reaction mixture was concentrated to an off white residue
  2. customThe residue was triturated with ethyl acetate
  3. customdried overnight in vacuo

Sources & evidence

ORD record
ord-7889b786ad9745c6a683b2c676901b24
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

Loading…