HCID 20671782, compound → HCID 86757170, compound

HRID 1385913Notes

Reaction equation

HRID 1385913 reaction equation
[CH3:1][N:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:15][C:16]([OH:18])=[O:17])[O:3]1.[C:19](OC(=N)N(C(C)C)C(C)C)([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl.Cl[Cu]>[CH3:1][N:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[O:3]1

Participants

5

Reactant 2

HCID 20671782HCID 20671782, compoundHCID 22010542tert-Butyl N,N-dipropan-2-ylcarbamimidate

Product 1

HCID 86757170HCID 86757170, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-methyl-3(S)-(4-cyanophenyl)-isoxazolidin-5(R)-yl]acetic acid (480 mg, 1.95 mmol) in CH2Cl2 (30 ml) cooled in an ice-water bath was added a 1.6M solution of O-tert-butyl-N, N-diisopropylisourea, cat. CuCl (3.7 ml). The resulting mixture was stirred at rt for 48 hrs. After filtration, the fitrate was concentrated in EtOAc and the residue dissolved in EtOAc. The EtOAc solution was washed with brine and then dried over Na2SO4. After contration, the residue was chromatographed with a mixture of EtOAc and hexane to afford 550 mg of the product as a white solid (93%). 1H NMR (300 MHz, CDCl3) δ1.44(s, 9H), 1.98(m, 1H), 2.50(dd, 1H), 2.60(s, 3H), 2.80(dd, 1H), 2.98(dt, 1H), 3.70(t, 1H), 4.64(m, 1H), 7.50(d, 2H0, 7.66(d, 2H); MS(ESI) Calc. for (M+1)+: 303. Found: 303.

Workup

  1. filtrationAfter filtration
  2. concentrationthe fitrate was concentrated in EtOAc
  3. dissolutionthe residue dissolved in EtOAc
  4. washThe EtOAc solution was washed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter contration, the residue was chromatographed with a mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-bf7d8ab3189b4e709ac22db2e258da80
Source dataset
uspto-grants-2001_07
Patent number
US06265400B1

Reaction notes

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