Hydrochloric Acid → HCID 178463212, compound

HRID 1527796Notes

Reaction equation

HRID 1527796 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-6a65d9d6974a4c508fbb813bb380528c
Source dataset
uspto-grants-2015_07
Patent number
US09089575B2

Reaction notes

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