Hydrochloric Acid → HCID 178484745, compound

HRID 216080Notes

Reaction equation

HRID 216080 reaction equation
[CH3:1][N:2]([CH3:53])[C:3]([O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2([CH2:28][C:29]3[N:30]=[CH:31][N:32](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:33]=3)[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[O:14])[CH:9]=[CH:10][CH:11]=1)=[O:4].Cl>CO>[CH3:53][N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:15]2([CH2:28][C:29]3[N:30]=[CH:31][NH:32][CH:33]=3)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[O:14])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68992070tert-butyl 4-(3-(dimethylcarbamoyloxy)-phenylcarbamoyl)-4-((1-trityl-1H-imidazol-4-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 178484745HCID 178484745, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-(3-(dimethylcarbamoyloxy)-phenylcarbamoyl)-4-((1-trityl-1H-imidazol-4-yl)methyl)piperidine-1-carboxylate from step C (180 mg) in MeOH (5 mL) was added HCl (1 N in dioxane, 1 mL). The reaction was heated at 60° C. for 1 hour, and then concentrated under vacuum. The residue was dissolved in EtOAc (5 mL), washed with aq. NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under vacuum to produce the title compound (84 mg, 93%). MS (ES+) [M+H]+=372.2.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in EtOAc (5 mL)
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0b84828691b84904852ea8e0afea80cd
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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