Hydrochloric Acid → HCID 178507187, compound

HRID 748640Notes

Reaction equation

HRID 748640 reaction equation
C(OC([NH:8][C:9]1[C:14]([Br:15])=[CH:13][C:12]([Br:16])=[CH:11][C:10]=1[CH2:17][NH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([O:25][C:26](=[O:34])[CH2:27][CH2:28][CH2:29][O:30][N+:31]([O-:33])=[O:32])[CH2:21][CH2:20]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[NH2:8][C:9]1[C:14]([Br:15])=[CH:13][C:12]([Br:16])=[CH:11][C:10]=1[CH2:17][NH:18][C@H:19]1[CH2:20][CH2:21][C@H:22]([O:25][C:26](=[O:34])[CH2:27][CH2:28][CH2:29][O:30][N+:31]([O-:33])=[O:32])[CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452622HCID 178452622, compound

Product 1

HCID 178507187HCID 178507187, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(nitroxy)butyric acid 4-[(2-tert-butoxycarbonylamino-3,5-dibromophenyl)methylamino]trans cyclohexyl ester (3.5 g, 5.74 mmoles) in ethyl acetate (100 ml), cooled at 0° C., a 5N HCl solution in ethyl acetate (5.95 ml) is added. The solution is maintained under stirring at 0° C. for 5 hours, then filtered. The obtained solid is suspended in ethyl acetate and the organic layer washed with a 5% sodium carbonate solution. The organic phase is washed with water, anhydrified with sodium sulphate and evaporated at reduced pressure. The residue is purified by chromatography on silica gel, eluting with n-hexane/ethyl acetate 1/1 (ratio by volume). 4-(nitroxy)butyric acid 4-[(2-amino-3,5-dibromophenyl)methylamino]trans cyclohexyl ester is obtained. Yield 31%.

Workup

  1. temperatureThe solution is maintained
  2. filtrationfiltered
  3. washthe organic layer washed with a 5% sodium carbonate solution
  4. washThe organic phase is washed with water
  5. customevaporated at reduced pressure
  6. customThe residue is purified by chromatography on silica gel
  7. washeluting with n-hexane/ethyl acetate 1/1 (ratio by volume)

Sources & evidence

ORD record
ord-834227e347df4463a36bfd1b590cfb1f
Source dataset
uspto-grants-2008_07
Patent number
US07399878B2

Reaction notes

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