Hydrochloric Acid → HCID 86711982, compound

HRID 2281048Notes

Reaction equation

HRID 2281048 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:18]4[CH:31]=[CH:30][C:21]([CH2:22][NH:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=4)=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.Cl.[O-:33][C:34]#[N:35].[K+].C(=O)(O)[O-].[Na+]>O.ClCCl>[C:34]([N:23]([CH2:22][C:21]1[CH:30]=[CH:31][C:18]([C:12]2[CH:11]=[CH:10][C:9]3[N:5]([CH2:4][CH:1]4[CH2:2][CH2:3]4)[N:6]=[N:7][C:8]=3[C:13]=2[C:14]([F:15])([F:16])[F:17])=[CH:19][CH:20]=1)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:33])[NH2:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 70978060HCID 70978060, compound

Product 1

HCID 86711982HCID 86711982, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl N-{4-[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]benzyl}glycinate (42 mg, 0.097 mmol) was added to a dichloromethane:1 N hydrochloric acid solution (400 μL:80 μL) and the mixture placed into an ice-bath at 0° C. Potassium cyanate (24 mg, 0.29 mmol) was dissolved in deionized water (300 uL) and this solution was added to the mixture over 5 minutes. The mixture was vigorously stirred for 1.5 hours, at which time the mixture was treated with sodium bicarbonate (aqueous saturated) and extracted with ethyl acetate (3×40 mL). The organic layers were combined, dried with sodium sulfate, filtered and concentrated in vacuo to provide the titled compound.

Workup

  1. additionthis solution was added to the mixture over 5 minutes
  2. extractionextracted with ethyl acetate (3×40 mL)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8b6deed73c24c86937e947de022e2b9
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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