Cyanuric chloride → benzyl N-[(1S,3R)-3-cyanocyclohexyl]carbamate

HRID 75003

Reaction equation

HRID 75003 reaction equation
[C:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5]1)(=O)[NH2:2].ClC1N=C(Cl)N=C(Cl)N=1>CN(C=O)C.[Au]>[C:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:5]1)#[N:2]

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 68007396Benzyl ((1S,3R)-3-carbamoylcyclohexyl)carbamate2×

Product 1

HCID 23584440benzyl N-[(1S,3R)-3-cyanocyclohexyl]carbamate

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate, 18d, (0.69 g, 2.50 mmol) in DMF (10 mL) at 0° C. was treated with 2,4,6-trichloro-1,3,5-triazine (0.61 g, 3.29 mmol) and allowed to stir while slowly warming to room temperature. After 20 minutes, the solution became gold in color. After 1 hour a precipitate had formed. Stirred for an additional 3 hours then quenched with ice water (100 mL) and extracted with CH2Cl2 (2×125 mL) then washed with 1N HCl (100 mL). The organic layer was concentrated in vacuo to afford an 730 mg of a residue that was purified using a pad of silica gel (45 mL) using 30% EtOAc/hexanes as eluent to afford 621 mg of a white solid after vacuum drying.

Workup

  1. customAfter 1 hour a precipitate had formed
  2. stirringStirred for an additional 3 hours
  3. customthen quenched with ice water (100 mL)
  4. extractionextracted with CH2Cl2 (2×125 mL)
  5. washthen washed with 1N HCl (100 mL)
  6. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-7df5f10e158b453f9a8878bd1a479995
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Linked notes

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