Carbon Tetrachloride → dibenzyl 3-(2,3-dihydro-1H-inden-5-yl)-6-isopropyl-2-oxo-4-thioxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-7-yl phosphate

HRID 402746Notes

Reaction equation

[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:15](=[S:16])[C:14]4[CH:17]=[C:18]([CH:22]([CH3:24])[CH3:23])[C:19]([OH:21])=[CH:20][C:13]=4[O:12][C:11]3=[O:25])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(Cl)(Cl)(Cl)Cl.C(N(C(C)C)CC)(C)C.[PH:40](=[O:57])([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(#N)C.CN(C)C1C=CN=CC=1>[P:40]([O:21][C:19]1[C:18]([CH:22]([CH3:23])[CH3:24])=[CH:17][C:14]2[C:15](=[S:16])[N:10]([C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[CH2:1][CH2:2][CH2:3]4)[C:11](=[O:25])[O:12][C:13]=2[CH:20]=1)([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:57]

Participants

Conditions

Temperature: 5 °C

Procedure

To a stirred solution of 0.30 g (0.84 mmols) of 5 in 10 mL of anhydrous acetonitrile at 5° C., was added 0.4 mL (4.24 mmols) of CCl4, 0.31 mL (1.78 mmols) of diisopropylethylamine and 10 mg (85□mols) of 4-dimethylaminopyridine in that order. After stirring the mixture for 5 min. at 5° C., 0.34 mL (1.27 mmols) of dibenzyl phosphonate 6 was added drop wise and the mixture stirred for 1 h at 5° C. The reaction was quenched with water, extracted the product with ethyl acetate and organic layers were washed with water and brine. Filtration of the product through a plug of silica gel afforded 0.52 g of the product 7 as brown liquid.

Workup

stirringthe mixture stirred for 1 h at 5° C
customThe reaction was quenched with water
extractionextracted the product with ethyl acetate and organic layers
washwere washed with water and brine
filtrationFiltration of the product through a plug of silica gel

Sources & evidence

ORD record: ord-720c8431c8cc4d0fb804ee1b7530cd84
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742133B2

Reaction notes

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