m-Chloroperbenzoic acid → Benzyl 1-(di-tert-butoxyphosphoryloxy)-2-phenylpropan-2-ylcarbamate

HRID 605406Notes

Reaction equation

[OH:1][CH2:2][C:3]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:4].C(N(CC)[P:25]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])C.N1C=NN=N1.ClC1C=C(C=CC=1)C(OO)=[O:48]>C1COCC1.ClCCl>[C:32]([O:31][P:25]([O:1][CH2:2][C:3]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:4])([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:48])([CH3:33])([CH3:34])[CH3:35]

Participants

Conditions

Temperature: -45 °C

Procedure

The product of Example 442A (2.7 mmol), di-tert-butyl diethylphosphoramidite (0.80 mL, 2.7 mmol), and 1-H-tetrazole (0.50 g, 6.8 mmol) in THF (25 mL) were reacted at room temperature for 12 hours. Subsequently the reaction was diluted with dichloromethane (25 mL) and cooled to −45° C. and followed by treatment with meta-chloroperoxybenzoic acid (0.66 g, 3.0 mmol) for 0.5 hours. The reaction was extracted with ethyl acetate (70 mL) and the organic extracts washed with 10% sodium carbonate (2×) and brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica gel, eluting with a gradient of ethyl acetate in dichloromethane (0-25%) to give the title compound as a colorless oil (0.99 g, 78%).

Workup

extractionThe reaction was extracted with ethyl acetate (70 mL)
washthe organic extracts washed with 10% sodium carbonate (2×) and brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by chromatography on silica gel
washeluting with a gradient of ethyl acetate in dichloromethane (0-25%)

Sources & evidence

ORD record: ord-0d501ab76d374a3987efbc9073eccad9
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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