Water → HCID 73895619, compound

HRID 2308210Notes

Reaction equation

HRID 2308210 reaction equation
O.C(=O)([O-])[O-].[Mg+2].[N:7]#[C:8]Br.[CH2:10]([O:17][C:18](=[O:32])[C@H:19]([CH2:28][CH:29]([CH3:31])[CH3:30])[NH:20][C:21](=[O:27])[C@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C.C(OCC)C>[CH2:10]([O:17][C:18](=[O:32])[C@H:19]([CH2:28][CH:29]([CH3:30])[CH3:31])[NH:20][C:21](=[O:27])[C@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:8]#[N:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10476Cyanogen Bromide2×HCID 11029Magnesium CarbonateHCID 86590469HCID 86590469, compound

Product 1

HCID 73895619HCID 73895619, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 10 mL diethyl ether, 2 mL water, and 150 mg magnesium carbonate was cooled in an ice bath and 0.83 mL (4.16 mmol) 5M cyanogen bromide in acetonitrile was added with stirring. A solution of (D)-prolyl-leucine benzyl ester (883 mg, 2.77 mmol) in 17 mL diethyl ether was added over the course of 10 minutes. Another 0.20 mL (1.0 mmol) of 5M cyanogen bromide in acetonitrile was then added and the mixture was stirred at room temperature for 30 minutes. The organic phase was decanted and the aqueous phase extracted twice with diethyl ether. The combined ether phase was washed with 1N HCl, water, and saturated sodium bicarbonate, then dried over magnesium sulfate. Filtration and evaporation of solvent gave the crude product that was purified by flash chromatography on silica gel, eluting with 2% methanol/dichloromethane. N-cyano-(D)-prolyl-leucine benzyl ester (11) was isolated as a pale yellow oil.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customThe organic phase was decanted
  4. extractionthe aqueous phase extracted twice with diethyl ether
  5. washThe combined ether phase was washed with 1N HCl, water, and saturated sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration and evaporation of solvent
  8. customgave the crude product that
  9. customwas purified by flash chromatography on silica gel
  10. washeluting with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-b150133c7f5e431fa7cb55ce36001b15
Source dataset
uspto-grants-2004_12
Patent number
US06835727B2

Reaction notes

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