Hydrochloric Acid → HCID 178463212, compound

HRID 1469163Notes

Reaction equation

HRID 1469163 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([N:22](C(OC(C)(C)C)=O)[CH3:23])[CH2:18][CH2:17]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:14][CH3:15])[C@H:16]2[CH2:21][CH2:20][C@H:19]([NH:22][CH3:23])[CH2:18][CH2:17]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178463214HCID 178463214, compound

Product 1

HCID 178463212HCID 178463212, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (30 g, 62.24 mmol) in methanol (100 mL) at 0° C., methanolic HCl (500 mL) was added and reaction was stirred for 2 h at room temperature. After completion, reaction was concentrated to dryness. The residue was basified with Na2CO3 (aq.) to pH 8 and aqueous layer was extracted with 10% methanol in DCM (200 mL×3). Combined organic layers were dried over Na2SO4 and solvent removed under reduced pressure to afford the title compound as colorless oil (25 g, crude). The isolated compound was used in the next step without further purification.

Workup

  1. customreaction
  2. customAfter completion, reaction
  3. concentrationwas concentrated to dryness
  4. extractionwas extracted with 10% methanol in DCM (200 mL×3)
  5. dry with materialCombined organic layers were dried over Na2SO4 and solvent
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-6a60ed99747a42f495146ceff710117a
Source dataset
uspto-grants-2015_04
Patent number
US09006242B2

Reaction notes

Loading…