Ammonia → HCID 178453949, compound

HRID 1984926Notes

Reaction equation

HRID 1984926 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:20](CC)CC)C.ClC(OCC)=O.N>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([C:15](=[O:17])[NH2:20])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178453971HCID 178453971, compound

Product 1

HCID 178453949HCID 178453949, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution cooled at 0° C. of cis-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (68.0 g, 280 mmol) and triethylamine (31.1 g, 307 mmol) in THF (300 mL) was added ethyl chloroformate (29.3 mL, 308 mmol) dropwise. After stirring at 0° C. for 30 min, 25% aqueous ammonia (168 mL) was added dropwise. The reaction mixture was stirred at ambient temperature for 2 hr and concentrated. The residue was extracted with EtOAc (three times). The combined organic layer was washed with saturated aqueous NaHCO3, 1 M HCl, brine, and water, dried over Na2SO4, filtered, and concentrated to give cis-(4-carbamoyl-cyclohexyl)-carbamic acid tert-butyl ester (62.0 g, 88%) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 2 hr
  2. concentrationconcentrated
  3. extractionThe residue was extracted with EtOAc (three times)
  4. washThe combined organic layer was washed with saturated aqueous NaHCO3, 1 M HCl, brine, and water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-77957949cc954f78a29914888fad1d08
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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