HCID 10944250, compound → HCID 86757171, compound

HRID 1385915Notes

Reaction equation

HRID 1385915 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][C@H:12]([CH2:14][C:15]([OH:17])=[O:16])[O:11][N:10]=2)=[CH:5][CH:4]=1)#[N:2].[C:18](OC(=N)N(C(C)C)C(C)C)([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl.Cl[Cu]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:13][C@H:12]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[O:11][N:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 10944250HCID 10944250, compoundHCID 22010542tert-Butyl N,N-dipropan-2-ylcarbamimidate

Product 1

HCID 86757171HCID 86757171, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of [3-(4-cyanophenyl)isoxazolin-5(R)-yl]acetic acid(500 mg, 2.17 mmol) in CH2Cl2 (20 ml) cooled in an ice-water bath was added a 1.6M solution of O-tert-butyl-N, N-diisopropylisourea, cat. CuCl(4 ml). The resulting mixture was stirred at rt for 48 hrs and then filted. The fitrate was concentrated and the residue dissolved in EtOAc. The EtOAc solution was washed with brine and then dried over Na2SO4. After concentration, the residue was chromatographed with a mixture of EtOAc and hexane to afford 600 mg of the product as a white solid(96%). 1H NMR(300 MHz, CDCl3) δ1.48(s, 9H), 2.60(dd, 1H), 2.60(dd, 1H), 3.16(dd, 1H), 3.52(dd, 1H), 5.169m, 1H0, 7.70(d, 2H), 7.78(d, 2H); MS(ESI) Calc. for (M−1)+: 285. Found: 285.

Workup

  1. temperaturecooled in an ice-water bath
  2. concentrationThe fitrate was concentrated
  3. dissolutionthe residue dissolved in EtOAc
  4. washThe EtOAc solution was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue was chromatographed with a mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-6f394d43cefd4a078a25942c074df9a6
Source dataset
uspto-grants-2001_07
Patent number
US06265400B1

Reaction notes

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