Triphenylphosphine → Tert-butyl-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenylcarbamate

HRID 2251320Notes

Reaction equation

O[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:16])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:38]=1[C:44]1[C:48]([CH2:49][OH:50])=[C:47]([CH:51]([CH3:53])[CH3:52])[O:46][N:45]=1>ClCCl>[C:11]([O:10][C:9](=[O:15])[N:8]([O:50][CH2:49][C:48]1[C:44]([C:38]2[C:37]([Cl:36])=[CH:42][CH:41]=[CH:40][C:39]=2[Cl:43])=[N:45][O:46][C:47]=1[CH:51]([CH3:53])[CH3:52])[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[CH3:16])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl 4-hydroxy-2-methylphenylcarbamate (3.0 g, 13.4 mmol), triphenylphosphine (3.53 g, 13.4 mmol), and [3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methanol (3.85 g, 13.4 mmol) in dichloromethane (40 mL) at 0° C. was treated with a solution of diisopropylazidodicarboxylate (2.65 mL, 13.4 mmol) in dichloromethane (10 mL) dropwise. The reaction was allowed to stir at 0° C. for 30 minutes, then warmed to ambient temperature for 1 h after which time the solvent was removed in vacuo. The resulting oil was chromatographed on silica gel eluting with 20% ethyl acetate/hexanes. Yield=4.34 g (66%) of tert-butyl 4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenylcarbamate.

Workup

temperaturewarmed to ambient temperature for 1 h after which time the solvent
customwas removed in vacuo
customThe resulting oil was chromatographed on silica gel eluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-dd615b75d177487f9ba7d76cd969987b
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319109B2

Reaction notes

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