Ammonia → HCID 178453949, compound

HRID 1896239Notes

Reaction equation

HRID 1896239 reaction equation
C(Cl)(=O)C(C)(C)C.[CH3:8][C:9]([CH3:24])([O:11][C:12]([NH:14][C@@H:15]1[CH2:20][CH2:19][C@H:18]([C:21](O)=[O:22])[CH2:17][CH2:16]1)=[O:13])[CH3:10].[NH3:25]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:9]([O:11][C:12](=[O:13])[NH:14][C@H:15]1[CH2:20][CH2:19][C@@H:18]([C:21](=[O:22])[NH2:25])[CH2:17][CH2:16]1)([CH3:24])([CH3:10])[CH3:8]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 62493Pivaloyl chlorideHCID 178453971HCID 178453971, compound

Product 1

HCID 178453949HCID 178453949, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

Pivaloyl chloride (0.36 ml, 2.96 mmol) was added to a solution of cis-4-[[(1,1-dimethylethoxy)carbonyl]amino]-cyclohexanecarboxylic acid (600 mg, 2.47 mmol) in CHCl3 (10 ml), triethylamine (0.7 ml) at 0° C. and stirred for 1 h. Then aqueous ammonia was added to the reaction mixture and stirred for 1 h. After completion of reaction, the reaction mixture was diluted with CHCl3 (2×25 ml). The organic layer was washed with saturated sodium bicarbonate solution, brine and dried over anhydrous sodium sulfate. The organic layer was concentrated under vacuum, the crude compound was washed with hexane (2×6 ml) and dried to afford 500 mg (91.8%) of cis-tert-butyl-4-carbamoylcyclohexylcarbamate as white color solid.

Workup

  1. stirringstirred for 1 h
  2. customAfter completion of reaction
  3. washThe organic layer was washed with saturated sodium bicarbonate solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under vacuum
  6. washthe crude compound was washed with hexane (2×6 ml)
  7. customdried

Sources & evidence

ORD record
ord-fec10eed74b1464bab060a92eb9aaed5
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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