Hydrochloric Acid → HCID 68517910, compound

HRID 1948370Notes

Reaction equation

HRID 1948370 reaction equation
[Si]([O:8][CH:9]1[CH:14]([NH:15][C:16]([C:18]2[NH:19][C:20]([CH3:25])=[C:21]([Cl:24])[C:22]=2[Cl:23])=[O:17])[CH2:13][CH2:12][N:11](C(OCC)=O)[CH2:10]1)(C(C)(C)C)(C)C.[OH-].[Na+].Cl>CO.O1CCOCC1>[Cl:23][C:22]1[C:21]([Cl:24])=[C:20]([CH3:25])[NH:19][C:18]=1[C:16]([NH:15][CH:14]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[OH:8])=[O:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 68517053HCID 68517053, compound2×

Product 1

HCID 68517910HCID 68517910, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl 3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidine-1-carboxylate (Intermediate 114, 0.805 g) was dissolved in a mixture of MeOH (10 mL) and 1,4-dioxane (15 mL), to which was added 1N NaOH (10 mL) and heated to reflux for twenty-four hours. An additional 5 mL of 1N NaOH was added, with 5 mL of 1,4-dioxane, and the reaction was heated for an additional forty-two hours, then cooled to 0° C. and acidified to ˜pH 9 with 2N HCl (6 mL). The cold mixture was filtered and washed with deionised water, yielding the title compound as a crude product. MS (ES) MH+: 292, 294 for C11H15Cl2N3O2.

Workup

  1. temperatureheated
  2. temperatureto reflux for twenty-four hours
  3. temperaturethe reaction was heated for an additional forty-two hours
  4. filtrationThe cold mixture was filtered
  5. washwashed with deionised water

Sources & evidence

ORD record
ord-4516a7acf06c4cdf8755536274dbc202
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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