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

HRID 884014Notes

Reaction equation

[OH:1][CH2:2][C:3]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])[CH3:4].C(N(CC)[P:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])C.N1C=NN=N1.C1C=C(Cl)C=C(C(OO)=[O:46])C=1>C1COCC1.ClCCl.C(OCC)(=O)C>[C:27]([O:26][P:20]([O:1][CH2:2][C:3]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])[CH3:5])([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:46])([CH3:28])([CH3:29])[CH3:30]

Participants

Conditions

Temperature: -45 °C

Procedure

The product of Example 95A (0.80 g, 3.8 mmol), di-tert-butyl diethylphosphoramidite (1.07 mL, 3.8 mmol), and 1-H-tetrazole (0.63 g, 8.99 mmol) in THF (35 mL) were reacted at room temperature for 12 hours. The reaction was diluted with dichloromethane (35 mL) and cooled to −45° C., and treated with mCPBA (0.90 g, 4.0 mmol) for 0.5 hours then diluted with ethyl acetate (100 mL). The organics were washed with 10% Na2CO3 (2×), 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 (0.926 g, 62%).

Workup

washThe organics were washed with 10% Na2CO3 (2×), 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-604db1b92fa64037aa616adf8ac20295
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236950B2

Reaction notes

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