tert-Butanol → HCID 68558515, compound

HRID 2362030Notes

Reaction equation

HRID 2362030 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]([CH2:14]C(O)=O)[CH2:12][O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C([N:20]([CH2:23]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])=CC=1.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:23](=[O:32])[NH:20][CH2:14][CH:13]1[CH2:12][O:11][N:10]=[C:9]1[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 44634450HCID 44634450, compound

Product 1

HCID 68558515HCID 68558515, compound

Conditions

Temperature
80 °C

Procedure

[3-(3,4-Dichloro-phenyl)-4,5-dihydro-isoxazol-4-yl]-acetic acid (1 eq) was added to warm tert-butanol (10 vol) at 30° C. Triethylamine (1 eq) was then added and the mixture stirred for 5 minutes. DPPA (1 eq) was then added and the mixture was heated to 80° C. for 1 day. The tert-butanol was concentrated, water (20 vol) was added and the organics extracted with EtOAc (15 vol). The organic phase was washed with a mixture of acidified (2N citric acid) water & brine (>10 vol), a mixture of saturated NaHCO3 and brine (10 vol), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash column chromatography (eluent: EtOAc:heptane) to yield [3-(3,4-Dichloro-phenyl)-4,5-dihydro-isoxazol-4-ylmethyl]-carbamic acid tert-butyl ester.

Workup

  1. concentrationThe tert-butanol was concentrated
  2. additionwater (20 vol) was added
  3. extractionthe organics extracted with EtOAc (15 vol)
  4. washThe organic phase was washed with a mixture
  5. additiona mixture of saturated NaHCO3 and brine (10 vol)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by flash column chromatography (eluent: EtOAc:heptane)

Sources & evidence

ORD record
ord-270f9e170c9d4de295e77f14a79321f0
Source dataset
uspto-grants-2014_04
Patent number
US08691824B2

Reaction notes

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